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Home> Encyclopedia >   /  Inorganic Chemicals  /  Organic Intermediates  /  Pharmaceuticals and Biochemicals  /  Pharmaceuticals and Biochemicals  /  Laboratory Chemicals
65277-42-1 structure

Ketoconazole

Iupac Name:2,2,2-trideuterio-1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
CAS No.:65277-42-1
EINECS(EC#): 265-667-4
Molecular Weight:534.452
Molecular Formula:C26H28Cl2N4O4 (isomer)
1. Names and Identifiers
1.1 Synonyms

(+-)-cis-1-Acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine (+)-Ketoconazole (+/-)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine (+/-)-cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine (2R,4S)-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine (2R,4S)-ketoconazole ,3-dioxolan-4-yl)methoxy)phenyl)-,cis- 1-(4-(4-(((2R,4S)-2-((1H-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethan-1-one 1-(4-(4-(((2R,4S)-2-((1H-IMIDAZOL-1-YL)METHYL)-2-(2,4-DICHLOROPHENYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZIN-1-YL)ETHANONE 1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone 142128-59-4 1-acetyl-4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine 24F2-1,25(OH)D3 277K421 65277-42-1 AB0090681 AB02344 AC-15957 AC1L9UG3 AKOS007930650 API0003081 BDBM60666 BDBM8610 BIDD:GT0696 BIM-0050645.0001 BPBio1_000635 BRD-K29113274-001-03-6 BRD-K29113274-001-11-9 BRD-K29113274-001-21-8 BRN 4303081 BSPBio_000577 C26H28Cl2N4O4 CAS-65277-42-1 CCG-100815 Certified Reference Material CHEBI:48336 CHEMBL75 CIS-1-ACETYL-4-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZINE cis-1-Acetyl-4-[4-[[2-(2,4- cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl] methoxy]phenyl]piperazine cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine CPD000058460 CS-1846 dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-piperazine DRG-0073 DSSTox_CID_9879 DSSTox_GSID_29879 DSSTox_RID_78829 DTXSID7029879 EI-107 EINECS 265-667-4 Ethanone, 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]- EU-0100666 Extina fungarest fungoral HMS1569M19 HMS2051A19 HMS2089N05 HMS2096M19 HMS2234H17 HMS3262E13 HMS3678J17 HMS3713M19 HSDB 7447 HY-B0105A J10202 K 1003 K0045 KCZ Ketocanazole ketoconazol Ketoconazole (k) Ketoconazole [USAN:INN:BAN:JAN] Ketoconazole 2.0 mg/ml in Methanol Ketoconazole, >=98% (HPLC) Ketoconazole, Antibiotic for Culture Media Use Only Ketoconazole, British Pharmacopoeia (BP) Reference Standard Ketoconazole, European Pharmacopoeia (EP) Reference Standard Ketoconazole, Pharmaceutical Secondary Standard Ketoconazole, United States Pharmacopeia (USP) Reference Standard Ketoconazole,(S) Ketoconazolum ketoderm ketoisdin KS-1205 KTN KTZ Kuric kw-1414 KZ Lopac0_000666 LP00666 LS-110149 MCULE-2726394491 MFCD00058579 MLS000069784 MLS000758224 MLS001146934 MLS001423987 MLS002207053 MLS002222255 MRF-0000100 NC00065 NCGC00016907-01 NCGC00025000-01 NCGC00025000-02 NCGC00025000-03 NCGC00025000-04 NCGC00025000-05 NCGC00025000-06 NCGC00025000-07 NCGC00025000-08 NCGC00025000-09 NCGC00025000-10 NCGC00253967-01 NCGC00261351-01 nizoral NSC 317629 Opera_ID_397 Piperazine, (+)-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]- Piperazine, (+/-)-1-acetyl-4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, rel- Prestwick_744 Prestwick0_000389 Prestwick1_000389 Prestwick2_000389 Prestwick3_000389 Q-201267 R 41,400 R 41400 R41,400 R41400 R-41400 rac-trans-Ketoconazole s1353 SAM001246983 SCHEMBL8407 SMR000058460 SPBio_002498 SR-01000075626 SR-01000075626-1 SR-01000075626-4 SR-01000597381 SR-01000597381-1 SR-01000597381-6 ST2407064 SW196888-4 Tocris-1103 Tox21_110676 Tox21_300267 Tox21_500666 UNII-R9400W927I component XMAYWYJOQHXEEK-OZXSUGGESA-N UPCMLD-DP138 UPCMLD-DP138:001 US9150527, Ketoconazole W-2941 Xolegel ZINC643138

1.2 Inchi
InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1/i1D3
1.3 InChkey
XMAYWYJOQHXEEK-SIULDFEJSA-N
1.4 Canonical Smiles
CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
1.5 Isomers Smiles
CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=
C5)Cl)Cl
2. 3D Conformer
3. Properties
3.1 Appearance
white to off white crystalline powder
3.2 Density
139.11 cm3
3.3 Melting Point
146℃
3.4 Boiling Point
753.4 °C at 760 mmHg
3.5 Vapour
6.41X10-14 mm Hg at 25 deg C (est)
3.6 Refractive Index
-10.5 ° (C=0.4, CHCl3)
3.7 Flash Point
409.4 °C
3.8 Solubility
Insoluble
3.9 Color/Form
white to light yellow
3.10 Other physical and chemical properties
COLOURLESS CRYSTALS OR POWDER.
3.11 Stability
Stable at room temperature in closed containers under normal storage and handling conditions.
3.11 Stability
3.12 HS Code
2933990090
3.13 Storage temp
2-8°C
4. Safety and Handling
4.1 Hazard Codes
T
4.1 Risk Statements
R25
4.2 Safety Statements
S36;S45
4.3 HazardClass
6.1(b)
4.4 Hazard Note
H301; H360F; H373; H410
4.5 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TK7912300
CHEMICAL NAME :
Piperazine, 1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-imidazol -1-ylmethyl)-1,3-diox olan- 4-yl)methoxy)phenyl)-, cis-
CAS REGISTRY NUMBER :
65277-42-1
LAST UPDATED :
199612
DATA ITEMS CITED :
31
MOLECULAR FORMULA :
C26-H28-Cl2-N4-O4
MOLECULAR WEIGHT :
531.48
WISWESSER LINE NOTATION :
T6N DNTJ AV1 DR DO1- DT5O COTJ BR BG DG& B1- AT5N CNJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
45 mg/kg/17D-I
TOXIC EFFECTS :
Behavioral - coma Liver - jaundice, other or unclassified
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
412 mg/kg/15W-I
TOXIC EFFECTS :
Behavioral - coma Liver - hepatitis (hepatocellular necrosis), diffuse Liver - jaundice, other or unclassified
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
264 mg/kg/66D-I
TOXIC EFFECTS :
Liver - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
450 mg/kg/90D-I
TOXIC EFFECTS :
Endocrine - evidence of thyroid hypofunction Nutritional and Gross Metabolic - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
49 mg/kg/17D-I
TOXIC EFFECTS :
Liver - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
60 mg/kg
TOXIC EFFECTS :
Liver - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
166 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1474 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
86 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
618 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2937 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
32 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
178 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
23300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
178 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
23300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1200 mg/kg/30D-I
TOXIC EFFECTS :
Liver - other changes Liver - changes in liver weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1029 mg/kg
SEX/DURATION :
male 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male Endocrine - androgenic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6480 mg/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles) Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
600 mg/kg
SEX/DURATION :
male 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3240 mg/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating - 7 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 - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
880 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1040 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
300 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
300 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
520 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Cells - not otherwise specified
DOSE/DURATION :
1 umol/L
REFERENCE :
TUMOAB Tumori. (Casa Editrice Ambrosiana, Via G. Frua 6, 20146 Milan, Italy) V.1- 1911- Volume(issue)/page/year: 77,385,1991 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6059 No. of Facilities: 30 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 1045 (estimated) No. of Female Employees: 620 (estimated)
4.6 PackingGroup
III
4.7 Transport
UN 2811
4.8 Formulations/Preparations
Tablets as 0.2 g; 2% solutions, ointments, and cream preparations.
Trade Names: Candoral, Cetonax, Fitonal, Fungarest, Fungicil, Fungo-Hubber, Fungoral, Ketazol, Ketoderm, Ketoisdin, Ketonan, Ketoral, Micoral, Micotek, Micoticum, Nizoral, Nizshampoo, Oromycosal, Oronazol, Panfungol, Rofenid, Terzolin.
Topical: Cream 2% Ketoconazole, (Taro, Teva), Shampoo: 1 Nizoral A-D, (McNeil), 2% Nizoral, (McNeil).
Oral: Tablets: 200 mg Ketoconazole Tablets (scored), AAIPharma, Mutual, Mylan, Sidmak, Pliva, Taro, Teva, Torpharm); Nizoral ( with povidone; scored), (Janssen).
4.9 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl ketoconazole, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
4.10 Octanol/Water Partition Coefficient
log Kow = 4.34
4.11 Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Specific target organ toxicity \u2013 repeated exposure, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

H410 Very toxic to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P273 Avoid release to the environment.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

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

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

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

P330 Rinse mouth.

P314 Get medical advice/attention if you feel unwell.

P391 Collect spillage.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Computational chemical data
  • Molecular Weight:534.452g/mol
  • Molecular Formula:C26H28Cl2N4O4
  • Compound Is Canonicalized:True
  • XLogP3-AA:4.3
  • Exact Mass:533.168
  • Monoisotopic Mass:533.168
  • Complexity:735
  • Rotatable Bond Count:7
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:6
  • Topological Polar Surface Area:69.1A^2
  • Heavy Atom Count:36
  • Defined Atom Stereocenter Count:2
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:3
  • Covalently-Bonded Unit Count:1
  • CACTVS Substructure Key Fingerprint: AAADceB7uAAGAAAAAAAAAAAAAAAAAWJAAAA8YIAAAAAAAAAB0AAAHgIAAAAADB7hmiY/3pcMFACo AjV3dACCiC0xN6AJyAAefoifbiLFu5u3OCjtxhPe6CewwKAOBEAAAACBAAAIgAAAAQIAAAAAAAAA AA==
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