Ketoconazole

Modify Date: 2024-01-02 11:35:49

Ketoconazole structure	Common Name	Ketoconazole
	CAS Number	65277-42-1	Molecular Weight	531.431
	Density	1.4±0.1 g/cm3	Boiling Point	753.4±60.0 °C at 760 mmHg
	Molecular Formula	C₂₆H₂₈Cl₂N₄O₄	Melting Point	146°C
	MSDS	Chinese USA	Flash Point	409.4±32.9 °C
	Symbol	GHS06, GHS08, GHS09	Signal Word	Danger

Use of Ketoconazole

Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 and CYP24A1 inhibitor.Target: CYP3A4 CYP24A1Ketoconazole, an imidazole anti-fungal agent, has often produced features of androgen deficiency including decreased libido, gynecomastia, impotence, oligospermia, and decreased testosterone levels, in men being treated for chronic mycotic infections [1]. Ketoconazole also is a cytochrome P450 inhibitor [2].Ketoconazole (KTZ), on the antischistosomal potential of these quinolines against Schistosoma mansoni infection by evaluating parasitological, histopathological, and biochemical parameters. Mice were classified into 7 groups: uninfected untreated (I), infected untreated (II), infected treated orally with PZQ (1,000 mg/kg) (III), QN (400 mg/kg) (IV), KTZ (10 mg/kg)+QN as group IV (V), HF (400 mg/kg) (VI), and KTZ (as group V)+HF (as group VI) (VII). KTZ plus QN or HF produced more inhibition (P<0.05) in hepatic CYP450 (85.7% and 83.8%) and CYT b5 (75.5% and 73.5%) activities, respectively, than in groups treated with QN or HF alone. This was accompanied with more reduction in female (89.0% and 79.3%), total worms (81.4% and 70.3%), and eggs burden (hepatic; 83.8%, 66.0% and intestinal; 68%, 64.5%), respectively, and encountering the granulomatous reaction to parasite eggs trapped in the liver.[3] CYP24A1 inhibitor enhances antiproliferative effects, increases systemic calcitriol exposure, and promotes the activation of caspase-independent apoptosis pathway.[4]

Name	Ketoconazole
Synonym	More Synonyms

Description	Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 and CYP24A1 inhibitor.Target: CYP3A4 CYP24A1Ketoconazole, an imidazole anti-fungal agent, has often produced features of androgen deficiency including decreased libido, gynecomastia, impotence, oligospermia, and decreased testosterone levels, in men being treated for chronic mycotic infections [1]. Ketoconazole also is a cytochrome P450 inhibitor [2].Ketoconazole (KTZ), on the antischistosomal potential of these quinolines against Schistosoma mansoni infection by evaluating parasitological, histopathological, and biochemical parameters. Mice were classified into 7 groups: uninfected untreated (I), infected untreated (II), infected treated orally with PZQ (1,000 mg/kg) (III), QN (400 mg/kg) (IV), KTZ (10 mg/kg)+QN as group IV (V), HF (400 mg/kg) (VI), and KTZ (as group V)+HF (as group VI) (VII). KTZ plus QN or HF produced more inhibition (P<0.05) in hepatic CYP450 (85.7% and 83.8%) and CYT b5 (75.5% and 73.5%) activities, respectively, than in groups treated with QN or HF alone. This was accompanied with more reduction in female (89.0% and 79.3%), total worms (81.4% and 70.3%), and eggs burden (hepatic; 83.8%, 66.0% and intestinal; 68%, 64.5%), respectively, and encountering the granulomatous reaction to parasite eggs trapped in the liver.[3] CYP24A1 inhibitor enhances antiproliferative effects, increases systemic calcitriol exposure, and promotes the activation of caspase-independent apoptosis pathway.[4]
Related Catalog	Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450 Signaling Pathways >> Anti-infection >> Fungal Research Areas >> Infection
References	[1]. Seif El-Din SH, et al. Effect of ketoconazole, a cytochrome P450 inhibitor, on the efficacy of quinine and halofantrine against Schistosoma mansoni in mice. Korean J Parasitol. 2013 Apr;51(2):165-75. [2]. Eil C. Ketoconazole binds to the human androgen receptor. Horm Metab Res. 1992 Aug;24(8):367-70. [3]. Muindi JR et al. CYP24A1 inhibition enhances the antitumor activity of calcitriol. Endocrinology. 2010 Sep;151(9):4301-12.

Description

Related Catalog

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

References

[1]. Seif El-Din SH, et al. Effect of ketoconazole, a cytochrome P450 inhibitor, on the efficacy of quinine and halofantrine against Schistosoma mansoni in mice. Korean J Parasitol. 2013 Apr;51(2):165-75.

[2]. Eil C. Ketoconazole binds to the human androgen receptor. Horm Metab Res. 1992 Aug;24(8):367-70.

[3]. Muindi JR et al. CYP24A1 inhibition enhances the antitumor activity of calcitriol. Endocrinology. 2010 Sep;151(9):4301-12.

Density	1.4±0.1 g/cm3
Boiling Point	753.4±60.0 °C at 760 mmHg
Melting Point	146°C
Molecular Formula	C₂₆H₂₈Cl₂N₄O₄
Molecular Weight	531.431
Flash Point	409.4±32.9 °C
Exact Mass	530.148743
PSA	69.06000
LogP	3.55
Vapour Pressure	0.0±2.5 mmHg at 25°C
Index of Refraction	1.642

Ketoconazole MSDS(Chinese)

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)

Symbol	GHS06, GHS08, GHS09
Signal Word	Danger
Hazard Statements	H301-H360F-H373-H410
Precautionary Statements	P201-P273-P301 + P310-P308 + P313-P501
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T:Toxic;
Risk Phrases	R25
Safety Phrases	S36-S45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	TK7912300
Packaging Group	III
Hazard Class	6.1(b)
HS Code	2933990090

Imidazole

CAS#:288-32-4

(2R,4S)-cis-2-(...

CAS#:142128-67-4

~53%

Ketoconazole

CAS#:65277-42-1

(2R,4S)-cis-2-(...

CAS#:142004-25-9

Literature: Journal of Medicinal Chemistry, , vol. 35, # 15 p. 2818 - 2825

(2R,4S)-(+)-2-(...

CAS#:170210-42-1

Ketoconazole

CAS#:65277-42-1

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 4 p. 887 - 890

4-(1-Piperazino...

CAS#:56621-48-8

Ketoconazole

CAS#:65277-42-1

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 4 p. 887 - 890

Loratadine Side...

CAS#:133345-21-8

Ketoconazole

CAS#:65277-42-1

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 4 p. 887 - 890

cis-2-(2,4-dich...

CAS#:70894-66-5

Ketoconazole

CAS#:65277-42-1

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 4 p. 887 - 890

N/A

CAS#:170210-43-2

1-Acetyl-4-(4-h...

CAS#:67914-60-7

Ketoconazole

CAS#:65277-42-1

Literature: Tetrahedron: Asymmetry, , vol. 6, # 6 p. 1283 - 1294

Precursor 5
CAS#:288-32-4 Imidazole CAS#:170210-42-1 (2R,4S)-(+)-2-(... CAS#:56621-48-8 4-(1-Piperazino... CAS#:70894-66-5 cis-2-(2,4-dich...
CAS#:67914-60-7 1-Acetyl-4-(4-h...
DownStream 1
CAS#:38304-91-5 Minoxidil

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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(2R,4S)-ketoconazole

Brizoral

Ketoconazole

Onofin K

Nizral

Ethanone, 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]-

1-[4-(4-{[(4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethanone

Fitonal

1-[4-(4-{[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1-piperazinyl]ethanone

MFCD00058579

Fungarest

EINECS 265-667-4

1-[4-(4-{[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethanone

piperazine, 1-acetyl-4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-

1-Acetyl-4-(4-{[(2R,4S)-2-(2,4-dichlorphenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin

cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine

Fungoral

Ketoisdin

PANFUNGOL

Ketoderm

kw-1414

NIZORAL

Orifungal M

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Ketoconazole

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