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Home> Encyclopedia >Antibiotic and antimicrobial agents>Pharmaceutical Intermediates>Pharmaceuticals and Biochemicals
Cefixime structure
Cefixime structure

Cefixime

Iupac Name:(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS No.: 79350-37-1
Molecular Weight:453.45000
Modify Date.: 2022-10-30 20:03
Introduction: Cefixime is the first orally active third-generation cephalosponn with a true broadspectrum of activity. It is reportedly more effective against Gram-negative bacteria thanconventional oral cephems such as cephalexin and cefaclor. View more+
1. Names and Identifiers
1.1 Name
Cefixime
1.2 Synonyms

(6R,7R)-7-({(2-Amino-1,3-thiazol-4-yl)[(carboxymethoxy)imino]acetyl}amino)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (6R,7R)-7-[2-(2-AMINO-4-THIAZOLYL)GLOXYLAMIDO]-8-OXO-3-VINYL-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID, 72-(Z)-[O-(CARBOXYMETHYL)OXIME]TRIHYDRATE )(carboxymethoxy)imino)acetylamino)-3-ethenyl-8-oxo-,(6r-(6-alpha,7-beta(z))) 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-(2-amino-4-thiazolyl)-2-[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-, (6R,7R)- 8-[[2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-4-ethenyl-7-oxo-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid Cefixim CEFIXME TRIHYDRATE Cefspan CFIX cl284635 fk027 fr17027 MFCD03788802 Oroken Saprax Suprax Unixime YTTERBIUM(III) IONOPHORE I

1.3 CAS No.
79350-37-1
1.4 CID
5362065
1.5 EINECS(EC#)
616-684-4
1.6 Molecular Formula
C16H15N5O7S2 (isomer)
1.7 Inchi
InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1
1.8 InChkey
OKBVVJOGVLARMR-QSWIMTSFSA-N
1.9 Canonical Smiles
C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)C3=CSC(=N3)N)SC1)C(=O)O
1.10 Isomers Smiles
C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
2. Properties
2.1 Density
1.85 g/cm3
2.1 Melting point
218-225°C
2.1 Refractive index
1.811
2.1 Precise Quality
453.04100
2.1 PSA
238.05000
2.1 logP
0.36520
2.1 Solubility
55.11 mg/L
2.2 Appearance
white to off white powder or off white crystal powder
2.3 Storage
Hygroscopic, Refrigerator, Under Inert Atmosphere
2.4 Color/Form
Powder
2.5 Physical
Solid
2.6 pKa
pKa 2.10 (Uncertain)
2.7 Water Solubility
55.11 mg/L
2.8 StorageTemp
Hygroscopic, Refrigerator, Under Inert Atmosphere
3. Use and Manufacturing
3.1 Definition
ChEBI: A third-generation cephalosporin antibiotic bearing vinyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It is used in the treatment of gonorrhoea tonsilitis, pharyngitis, bronchitis, and urinary tract infections.
3.2 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 36 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 36 companies. For more detailed information, please visit ECHA C&L website

Of the 5 notification(s) provided by 35 of 36 companies with hazard statement code(s):

H315 (25.71%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (25.71%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H334 (28.57%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]
H335 (25.71%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501
3.3 Usage

Orally active, third generation cephalosporin antibiotic

4. Safety and Handling
4.1 Hazard Codes
Xn
4.1 Risk Statements
R42/43
4.1 Safety Statements
S22-S36/37-S45
4.1 WGK Germany
3
4.1 Safety
Hazard Codes:Xn
Risk Statements:42/43
42/43:May cause sensitization by inhalation and skin contact
Safety Statements:22-36/37-45
22:Do not breathe dust
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
WGK Germany:3
HS Code:38210000
4.2 Specification

The Cefixime, with the?CAS registry number 79350-37-1, has the IUPAC name of (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethyloxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Being a kind of white or light yellow crystalline powder with no odour, it is easily soluble in ethanol or dimethylsulfoxide, slightly soluble in acetone while insoluble in hexane, acetic acid or water. And its product categories are including Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds.

The physical properties of this chemical are as follows: (1)ACD/LogP: 1.00; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -3.61; (4)ACD/LogD (pH 7.4): -3.78; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 12; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 184.48; (13)Index of Refraction: 1.811; (14)Molar Refractivity: 105.6 cm3; (15)Molar Volume: 244.4 cm3; (16)Polarizability: 41.86×10-24 cm3; (17)Surface Tension: 89.9 dyne/cm; (18)Density: 1.85 g/cm3; (19)Exact Mass: 453.041289; (20)MonoIsotopic Mass: 453.041289; (21)Topological Polar Surface Area: 238; (22)Heavy Atom Count: 30; (23)Complexity: 861.

As to its usage, it is widely applied in many ways. It could be used in the third generation oral cephalosporins broad-spectrum antibiotic, with good antibacterial action to the streptococcus, Gram-negative bacteria, colibacillus, pneumobacillus, and proteus mirabilis. It could also be used to treat pharyngitis, gonorrhes and tonsilitis.
?
When you are dealing with this chemical, you should be much more cautious. For being a kind of harmful chemical, it may cause damage to health and may cause sensitisation by inhalation and skin contact. Therefore, you should wear suitable protective clothing and gloves and if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). Then do not breathe dust.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)C3=CSC(=N3)N)SC1)C(=O)O
(2)Isomeric SMILES: C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
(3)InChI: InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1
(4)InChIKey: OKBVVJOGVLARMR-QSWIMTSFSA-N?

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 3200mg/kg (3200mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: STRUCTURAL OR FUNCTIONAL CHANGES IN URETER
Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
dog LD50 oral > 600mg/kg (600mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
mouse LD50 intravenous 4420mg/kg (4420mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
mouse LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
rat LD50 intravenous 6990mg/kg (6990mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
rat LD50 oral > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 3509, 1986.

4.3 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XI0367200
CHEMICAL NAME :
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl) (carboxymethoxy)imino)acetylamino)-3-ethenyl-8-oxo-, (6R-(6-alpha,7-beta(Z)))-
CAS REGISTRY NUMBER :
79350-37-1
LAST UPDATED :
199612
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C16-H15-N5-O7-S2
MOLECULAR WEIGHT :
453.48

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea
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: 20,3509,1986
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)
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: 20,3509,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
6990 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold
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: 20,3509,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea
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: 20,3509,1986
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)
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: 20,3509,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4420 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold
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: 20,3509,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>600 mg/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea
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: 20,3509,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>3200 mg/kg
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting Kidney, Ureter, Bladder - structural or functional changes in ureter Nutritional and Gross Metabolic - weight loss or decreased weight gain
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: 20,3509,1986 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
371 gm/kg/53W-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes Endocrine - other changes Related to Chronic Data - death
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: 20,3509,1986
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H317 May cause an allergic skin reaction

Precautionary statement(s)
Prevention

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Synthesis Route
79350-37-1Total: 1 Synthesis Route
8. Precursor and Product
precursor:
88621-01-6
88621-01-6
9. Computational chemical data
  • Molecular Weight: 453.45000g/mol
  • Molecular Formula: C16H15N5O7S2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 453.04129018
  • Monoisotopic Mass: 453.04129018
  • Complexity: 861
  • Rotatable Bond Count: 8
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 12
  • Topological Polar Surface Area: 238
  • Heavy Atom Count: 30
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccB7uABgAAAAAAAAAAAAAABYAWAAAAAgAAAAAAAQAAABgAAAHgQUCAAADCjl1gahmRPYEgisAyXyfAIA8KlhCjkICJX4IFiLZJggxCEUEAAAFgKxkSAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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11. Realated Product Infomation