Nifedipine

Iupac Name：dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Molecular Weight：346.33462

Modify Date.: 2022-11-11 00:44

Introduction: Long-term coronary vasodilators. This product can increase coronary blood flow, reducing myocardial oxygen consumption.it is used for acute and chronic coronary insufficiency,especially the angina and myocardial infarction. View more+

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1. Names and Identifiers

1.1 Name: Nifedipine
1.2 Synonyms: 1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic Acid Dimethyl Ester 1,4-dihydro-2,6-diMethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate 1,4-Dihydro-2,6-dimethyl-4-(o-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl 2,6-Dimethyl-3,5-dicarbomethoxy-4-(2-nitrophenyl)-1,4-dihydropyridine 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester (9CI) 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(o-nitrophenyl)-, dimethyl ester (8CI) 4-(2'-nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridine 4-(2-Nitrophenyl)-2,6-dimethyl-3,5-dicarbomethoxy-1,4-dihydropyridine ADALAT Adalat CC ADALATE Adapress Aldipin ALDIPIN ANIFED Anifed Aprical Bonacid Camont Chronadalate Cordafen Cordaflex Cordicant Cordilan Cordipin Corinfar Corotrend Corynphar Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Dimethyl 4-(2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Dimethyl 4-(o-Nitrophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate Dimethyl-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridin-3,5-dicarboxylat Duranifin Ecodipin EINECS 244-598-3 Fenihidin Fenihidine Glopir Hexadilat Introcar Kordafen MFCD00057326 Nifedicor Nifedin Nifedipine (125 mg) Nifedipine,1,4-Dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester Nifelan Nifelat Nifelate Nifensar XL Niphedipine Niter benzene horizontal Orix Pidilat Procardia Procardia XL Sepamit Sepamit R Tibricol TN 873R Zenusin

1.3 CAS No.: 21829-25-4

1.4 CID: 4485

1.5 EINECS(EC#): 244-598-3

1.6 Molecular Formula: C17H18N2O6 (isomer)

1.7 Inchi: InChI=1S/C17H18N2O6/c1-9-13(16(20)24-3)15(14(10(2)18-9)17(21)25-4)11-7-5-6-8-12(11)19(22)23/h5-8,15,18H,1-4H3

1.8 InChkey: HYIMSNHJOBLJNT-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC

1.10 Isomers Smiles: CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC

2. Properties

2.1 Density: 1.271

2.1 Melting point: 171-175℃

2.1 Boiling point: 475.3 °C at 760 mmHg

2.1 Refractive index: 1.584

2.1 Flash Point: 241.2 °C

2.1 Precise Quality: 346.11600

2.1 PSA: 110.45000

2.1 logP: 3.02760

2.1 Solubility: DMSO: soluble

2.2 Appearance: Yellow Crystalline Solid

2.3 Storage: 2-8℃

2.4 Color/Form: Yellow powder

2.5 Decomposition: When heated to decomposition, it emits toxic fumes of /nitrogen oxides/.

2.6 pKa: pKa -0.9/>13(DMF,t undefined) (Uncertain)

2.7 Water Solubility: DMSO: soluble | <0.1 g/100 mL at 19.5 oC

2.8 Spectral Properties: UV max (methanol): 340, 235 nm (E 5010, 21590); (0.1N HCl): 338, 238 nm (E 5740, 20600); (0.1N NaOH): 340, 238 (E 5740, 20510)

2.9 Stability: Stable under normal temperatures and pressures.

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Produe Method: O-nitrobenzaldehyde, methyl acetoacetate, methanol, ammonia are refluxed together , then froze , crystallize,after filtration, nifedipine crude is obtained . The crude product is recrystallized through methanol .then the product is derived , yield rate is 50%.

3.2 Usage: Long-term coronary vasodilators. This product can increase coronary blood flow, reducing myocardial oxygen consumption.it is used for acute and chronic coronary insufficiency,especially the angina and myocardial infarction.

4. Safety and Handling

4.1 Symbol: GHS07;

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22

4.1 Safety Statements: S26;S36

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl nifedipine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

4.2 Octanol/Water Partition Coefficient: log Kow = 2.20

4.3 Fire Hazard: Flash point data for Nifedipine are not available; however, Nifedipine is probably combustible.

4.4 Hazard Class: IRRITANT

4.4 Hazard Declaration: H302

4.4 DisposalMethods: SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

4.5 RIDADR: US7975000

4.5 Caution Statement: P301 + P312 + P330

4.5 Formulations/Preparations: Adalat
Bay 1040
Bay A 1040
Citilat
Cordipin
Nifedin
Nifelat
Oxcord
Procardia

4.6 WGK Germany: 1

4.6 RTECS: US7975000

4.6 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: US7975000

CHEMICAL NAME :: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-, dimethyl ester

CAS REGISTRY NUMBER :: 21829-25-4

BEILSTEIN REFERENCE NO. :: 0497773

LAST UPDATED :: 199806

DATA ITEMS CITED :: 42

MOLECULAR FORMULA :: C17-H18-N2-O6

MOLECULAR WEIGHT :: 346.37

WISWESSER LINE NOTATION :: T6M DHJ B1 CVO1 DR BNW& EVO1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 34286 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - nausea or vomiting Gastrointestinal - necrotic changes

REFERENCE :: JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 33,725,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 105 mg/kg/26W-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 339,1382,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 2400 ug/kg/3D-I

TOXIC EFFECTS :: Behavioral - toxic psychosis

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 304,1225,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 11200 ug/kg

TOXIC EFFECTS :: Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: JJTOEX Japanese Journal of Toxicology. (Yakugyo Jihosha, Hokushin Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo, 101, Japan) V.1- 1988- Volume(issue)/page/year: 5,79,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 31 mg/kg/11W-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature increase

REFERENCE :: AHJOA2 American Heart Journal. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1925- Volume(issue)/page/year: 108,611,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 800 ug/kg/1D-I

TOXIC EFFECTS :: Brain and Coverings - changes in circulation (hemorrhage, thrombosis, etc.) Behavioral - headache Gastrointestinal - nausea or vomiting

REFERENCE :: PGMJAO Postgraduate Medical Journal. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1925- Volume(issue)/page/year: 62,1029,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1143 ug/kg/2D-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - toxic psychosis

REFERENCE :: AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 81,705,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 600 ug/kg/45M-I

TOXIC EFFECTS :: Vascular - BP lowering not characterized in autonomic section Gastrointestinal - nausea or vomiting

REFERENCE :: AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 147,556,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 8571 ug/kg

TOXIC EFFECTS :: Cardiac - change in rate Vascular - BP lowering not characterized in autonomic section

REFERENCE :: HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 9,309,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 143 ug/kg/1D

TOXIC EFFECTS :: Vascular - BP lowering not characterized in autonomic section

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,380,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 70 mg/kg

TOXIC EFFECTS :: Cardiac - cardiomyopathy including infarction Vascular - BP lowering not characterized in autonomic section Endocrine - hyperglycemia

REFERENCE :: PEDIAU Pediatrics. (American Academy of Pediatrics, P.O. Box 1034, Evanston, IL 60204) V.1- 1948- Volume(issue)/page/year: 86,91,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 714 ug/kg

TOXIC EFFECTS :: Cardiac - change in rate Vascular - BP lowering not characterized in autonomic section

REFERENCE :: AEMED3 Annals of Emergency Medicine. (American College of Emergency Physicians, 1125 Executive Circle, Irving, TX 75038) Volume(issue)/page/year: 22,196,1993

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1022 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,1,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 230 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 28,1451,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 5,1831,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 54,275,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 202 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3644627

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 185 mg/kg

TOXIC EFFECTS :: Vascular - BP lowering not characterized in autonomic section Vascular - regional or general arteriolar or venous dilation

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 16,817,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 5,1831,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4200 ug/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,1,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,1,1972

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 500 ug/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,1,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 504 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 35,915,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,1,1972 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4800 mg/kg/4W-I

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - urine volume increased Nutritional and Gross Metabolic - changes in potassium

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 5,1831,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 14400 mg/kg/24W-I

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - urine volume increased Nutritional and Gross Metabolic - changes in potassium

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 5,1831,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1152 mg/kg/12W-I

TOXIC EFFECTS :: Cardiac - changes in heart weight Liver - changes in liver weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 35,915,1985

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 91250 mg/kg/2Y-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 36(1,pt2),174,1997 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 200 ug/kg

SEX/DURATION :: female 27 week(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - other effects to embryo

REFERENCE :: GOBIDS Gynecologic and Obstetric Investigation. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.9- 1978- Volume(issue)/page/year: 24,151,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 200 ug/kg

SEX/DURATION :: female 33 week(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - other effects to embryo

REFERENCE :: BJOGAS British Journal of Obstetrics and Gynaecology. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.82- 1975- Volume(issue)/page/year: 100,959,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 550 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - stillbirth

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 19,2503,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10 mg/kg

SEX/DURATION :: female 21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

REFERENCE :: PEREBL Pediatric Research. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1967- Volume(issue)/page/year: 26,442,1989

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 40 mg/kg

SEX/DURATION :: female 14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 40,127,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 275 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21(Suppl 4),S1095,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 15 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: REPTED Reproductive Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1987- Volume(issue)/page/year: 11,207,1997

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 5 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21(Suppl 4),S1115,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 33200 ug/kg

SEX/DURATION :: female 16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 45,247,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 780 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility Reproductive - Effects on Newborn - live birth index (measured after birth)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21(Suppl 4),S1125,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 6 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

REFERENCE :: YHHPAL Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1953- Suspended 1966-78. Volume(issue)/page/year: 21,740,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 6 mg/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

REFERENCE :: YHHPAL Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1953- Suspended 1966-78. Volume(issue)/page/year: 21,740,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 94 ug/kg/30M-C

SEX/DURATION :: female 18 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Maternal Effects - other effects

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 157,1003,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6165 No. of Facilities: 26 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 766 (estimated) No. of Female Employees: 426 (estimated)

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

21829-25-4Total: 15 Synthesis Route

552-89-6 288 Suppliers

21829-25-4 333 Suppliers

Literatures:
Tetrahedron, , vol. 45, # 12 p. 3967 - 3974
Yield: null

105-45-3 237 Suppliers

552-89-6 288 Suppliers

21829-25-4 333 Suppliers

Literatures:
Siddaiah; Basha, G. Mahaboob; Rao, G. Padma; Prasad, U. Viplava; Rao, R. Suryachendra Synthetic Communications, 2012 , vol. 42, # 5 p. 627 - 634
Yield: ~92%

105-45-3 237 Suppliers

552-89-6 288 Suppliers

21829-25-4 333 Suppliers

80742-11-6

Literatures:
Goerlitzer; Buss Archiv der Pharmazie, 1981 , vol. 314, # 11 p. 938 - 949
Yield: null

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8. Precursor and Product

precursor:

126192-87-8

126192-88-9

105-45-3

21731-17-9

124732-83-8

552-89-6

1336-21-6

124732-84-9

14205-39-1

139445-58-2

product :

145655-14-7

34785-00-7

63675-72-9

21889-33-8

142271-31-6

50428-14-3

34783-31-8

67035-22-7

105378-62-9

145655-18-1

73372-63-1

145655-16-9

9. Other Information

9.0 Merck: 14,6528

9.1 Target: Value

9.2 Pharmacological effects: Nifedipine is a kind of dihydropyridine calcium antagonists, it can inhibit the Ca2 + uptake of cardiac and vascular smooth muscles, and it can expand the coronary artery , increase coronary blood flow,and improve myocardial ischemic tolerance, at the same time, it can expand peripheral arteries and reduce peripheral vascular resistance,and relieve coronary artery spasm, and increase coronary blood flow, improve myocardial ischemia,in order to decrease the blood pressure. Small doses do not affect blood pressure, when expanding coronary artery ,it is a better anti-angina drug .It is used for the prevention and treatment of angina pectoris,with no adverse effects on respiratory function, its efficacy is best particularly for angina pectoris coronary spasm and obstructive airway disease with angina , its efficacy is superior to β-blockers.It is also applied to all types of high blood pressure, including severe and resistant hypertension. Treatment of refractory congestive heart failure may be taking this long. It is also used for the treatment of primary pulmonary hypertension, diffuse esophageal spasm and bronchial asthma, duodenal ulcers, urinary tract obstruction, exercise-induced asthma, achalasia.
Nifedipine has a certain selectivity on vascular smooth muscles , the direct negative inotropic effect and denaturation effect on the heart are weak, systemic administration of it does not cause the heart rate slowing down ,on the contrary, the heart rate performances reflected increase.

9.3 Chemical properties: Yellow crystals. Melting point 172-174 ℃. Soluble in acetone, chloroform, ethyl acetate, dissolved in hot methanol, insoluble in water. It easily deteriorates in case of light.

9.4 Uses: Long-term coronary vasodilators. This product can increase coronary blood flow, reducing myocardial oxygen consumption.it is used for acute and chronic coronary insufficiency,especially the angina and myocardial infarction.

9.5 Production methods: O-nitrobenzaldehyde, methyl acetoacetate, methanol, ammonia are refluxed together , then froze , crystallize,after filtration, nifedipine crude is obtained . The crude product is recrystallized through methanol .then the product is derived , yield rate is 50%.

9.6 Category: Toxic substances

9.7 Toxicity grading: Highly toxic

9.8 Acute toxicity: Oral-rat LD50: 1022 mg/kg; Oral-Mouse LD50: 310 mg/kg.

9.9 Flammability and hazard characteristics: Combustion produces toxic fumes of nitrogen oxides; medicinal side effects: low blood pressure, cardiac disease, local blood flow disease, high blood sugar, psychosis.

9.10 Storage Characteristics: Ventilated , low-temperature, drying; and it is kept separately from food raw materials warehouse.

9.11 Extinguishing agent: Dry powder, foam, sand, carbon dioxide, water spray.

9.12 Chemical Properties: Yellow Crystalline Solid

9.13 Originator: Adalat,Bayer,W. Germany,1975

9.14 Uses: Used as an antihypertensive and antianginal. A dihydorpyridine calcium channel blocker

9.15 Uses: Nifedipine is used for preventing and relieving angina pectoris attacks, for hypertension, and as an ingredient in combination therapy for chronic cardiac insufficiency.

9.16 Uses: For the management of vasospastic angina, chronic stable angina, hypertension, and Raynaud's phenomenon. May be used as a first line agent for left ventricular hypertrophy and isolated systolic hypertension (long-acting agents).

9.17 Manufacturing Process: 45 grams 2-nitrobenzaldehyde, 80 cc acetoacetic acid methyl ester, 75 cc methanol and 32 cc ammonia are heated under reflux for several hours, filtered off, cooled and, after suction-filtration, 75 grams of yellow crystals of MP 172° to 174°C are obtained, according to US Patent 3,485,847.

9.18 Brand name: Adalat (Bayer); Afeditab (Watson);Procardia (Pfizer).

9.19 Therapeutic Function: Coronary vasodilator

9.20 World Health Organization (WHO): Nifedipine is a dihydropyridine calcium channel blocker. It is listed in the WHO Model List of Essential Drugs. The 10mg tablet is retained on the list for short-term treatment of hypertension. Sustained-release preparations are advised for long-term treatment.

9.21 General Description: Nifedipine, 1,4-dihydro-2, 6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylate dimethyl ester(Adalat, Procardia), is a dihydropyridine derivative thatbears no structural resemblance to the other calcium antagonists.It is not a nitrate, but its nitro group is essential for itsantianginal effect. As a class, the dihydropyridines possessa central pyridine ring that is partially saturated. To this, positions2 and 6 are substituted with an alkyl group that mayplay a role in the agent’s duration of action. In addition, positions3 and 5 are carboxylic groups that must be protectedwith an ester functional group. Depending on the type ofester used at these sites, the agent can be distributed to variousparts of the body. Finally, position 4 requires an aromaticsubstitution possessing an electron-withdrawinggroup (i.e., Cl or NO₂) in the ortho and/or meta position.

9.22 General Description: Odorless yellow crystals or powder. Tasteless.

9.23 Air & Water Reactions: Aqueous solutions are very sensitive to light. . Insoluble in water.

9.24 Reactivity Profile: Nifedipine is sensitive to light.

9.25 Fire Hazard: Flash point data for Nifedipine are not available; however, Nifedipine is probably combustible.

9.26 Biological Activity: L-type calcium channel blocker.

9.27 Biochem/physiol Actions: Nifedipine is a L-type Ca2+ channel blocker; and induces apoptosis in human glioblastoma cells. Nifedipine has neuroprotection activity and protects substantia nigra. Nifedipine has antioxidant potential. Nifedipine downregulates inflammatory cytokines like macrophage inflammatory protein-2 (MIP-2), tumor necrosis factor-α (TNF-α). Nifedipine has antihypertensive properties. Nifedipine inhibits extracellular region of adenosine A2a receptor (ADORA2A) gene.

9.28 Mechanism of action: Nifedipin causes relaxation of smooth musculature, dilation of coronary and peripheral arteries, and reduction of peripheral resistance and arterial blood pressure, and enhances oxygen supply to the heart.

9.29 Clinical Use: The prototype of this class, nifedipine, has potent peripheralvasodilatory properties. It inhibits the voltage-dependentcalcium channel in the vascular smooth muscle but has littleor no direct depressant effect on the SA or AV nodes, eventhough it inhibits calcium current in normal and isolated cardiactissues. Nifedipine is more effective in patients whoseanginal episodes are caused by coronary vasospasm and isused in the treatment of vasospastic angina as well as classicangina pectoris. Because of its strong vasodilatory properties,it is used in selected patients to treat hypertension.

9.30 Chemical Synthesis: Nifedipine, dimethyl ether 1,4-dihydro-2,6-dimethyl-4-(2′-nitrophenyl)-3,5- piridindicarboxylic acid (19.3.16), is synthesized by a Hantsch synthesis from two molecules of a β-dicarbonyl compound—methyl acetoacetate, using as the aldehyde component— 2-nitrobenzaldehyde and ammonia. The sequence of the intermediate stages of synthesis has not been completely established.

9.31 Usage: L-type calcium channel blocker; induces apoptosis in human glioblastoma cells.Nifedipine is a dihydropyridine calcium channel blocker used as L-type calcium channel blocker, antianginal and an antihypertensive . It induces apoptosis in human glioblastoma cells. It is used as a coronary vasodilator in the treatment of cardiac and circulatory disorders. Further, it is used in high-altitude medicine to treat high altitude pulmonary edema, hypertension and chronic stable angina. In addition, it is frequently used as a tocolytic agent.

10. Computational chemical data

Molecular Weight: 346.33462g/mol
Molecular Formula: C₁₇H₁₈N₂O₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 346.11648630
Monoisotopic Mass: 346.11648630
Complexity: 608
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 7
Topological Polar Surface Area: 110
Heavy Atom Count: 25
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB7OAAAAAAAAAAAAAAAAAAAAAAAAAAwQAAAAAAAAAABAAAAHgAUAAAADQiBmAIyyILQRACJAiTSSwCCAAAgAgAoiAEAZMoIJDKAsZGAMABkkACI6UeY/+megAAAAAACAAAAAAAAAAQAAAAAAAAAAA==

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