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Home> Hot Product Listed K   > Ketoconazole
79156-75-5 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.:79156-75-5
EINECS(EC#): 265-667-4
Molecular Weight:531.43100
Molecular Formula:C26H28Cl2N4O4 (isomer)
Names and Identifiers
Synonyms

1-[4-[4-[[2-(2 1-[4-[4-[[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]ethanone 1-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone 3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone 4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1 Nsc317629

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
InChkey
XMAYWYJOQHXEEK-SIULDFEJSA-N
Canonical Smiles
CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
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
Properties
Appearance
white to off white crystalline powder
Density
1.38 g/cm3
Melting Point
146ºC
Boiling Point
753.4ºC at 760 mmHg
Refractive Index
-10.5 ° (C=0.4, CHCl3)
Flash Point
409.4ºC
Solubility
Insoluble
Color/Form
white to light yellow
Other physical and chemical properties
COLOURLESS CRYSTALS OR POWDER.
Stability
Stable at room temperature in closed containers under normal storage and handling conditions.
Storage temp
2-8°C
Safety and Handling
Hazard Codes
T
Risk Statements
R25
Safety Statements
S36;S45
HazardClass
6.1(b)
Hazard Note
H301; H360F; H373; H410
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)
PackingGroup
III
Transport
UN 2811
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).
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.
Octanol/Water Partition Coefficient
log Kow = 4.34
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.
Computational chemical data
  • Molecular Weight:531.43100g/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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