Ciclopirox Olamine

Names

[ Name ]:
Ciclopirox Olamine

[Synonym ]:
2-aminoethanol,6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one compound with 2-aminoethanol
Terit
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone ethanolammonium salt
6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-on--2-aminoethanol(1:1)
Mycoster
MFCD00078997
2(1H)-Pyridinone, 6-cyclohexyl-1-hydroxy-4-methyl-, compd. with 2-aminoethanol (1:1)
6-Cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one - 2-aminoethanol (1:1)
Ciclochem
EINECS 255-464-9
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone - 2-aminoethanol (1:1)
Ciclopiroxolamine
Ciclopirox ethanolamine
Ciclopirox olamine
Ciclobirox olamine
6-cyclohexyl-1-hydroxy-4-méthylpyridin-2(1H)-one - 2-aminoéthanol (1:1)

Biological Activity

[Description]:

Ciclopirox olamine is a synthetic antifungal agent for topical dermatologic treatment of superficial mycoses. It is most useful against Tinea versicolor.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
350ºC at 760 mmHg

[ Melting Point ]:
144ºC

[ Molecular Formula ]:
C₁₄H₂₄N₂O₃

[ Molecular Weight ]:
268.352

[ Flash Point ]:
165.5ºC

[ Exact Mass ]:
268.178680

[ PSA ]:
88.48000

[ LogP ]:
2.07940

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UU7785500

CAS REGISTRY NUMBER :: 41621-49-2

LAST UPDATED :: 199806

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C12-H17-N-O2.C2-H7-N-O

MOLECULAR WEIGHT :: 268.40

WISWESSER LINE NOTATION :: T6NVJ AQ D1 F- AL6TJ &Z2Q

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 :: 2350 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 8,107,1977

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 146 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 9,57,1975

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2500 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,510,1995

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 72 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 8,107,1977

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1740 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 8,107,1977

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 83 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 9,57,1975

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1730 mg/kg

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

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 8,107,1977

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 71 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 9,57,1975

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >3065 mg/kg

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

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,1328,1981 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2800 mg/kg/4W-C

TOXIC EFFECTS :: Liver - other changes Gastrointestinal - other changes Related to Chronic Data - death

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 9,67,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1456 mg/kg/26W-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 28,115,1977

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
UU7785500

Articles

Comparison of the antifungal efficacy of terbinafine hydrochloride and ciclopirox olamine containing formulations against the dermatophyte Trichophyton rubrum in an infected nail plate model.

Mol. Pharm. 11(7) , 1991-6, (2014)

Onychomycosis is a fungal infection mostly induced by dermatophytes such as Trichophyton rubrum. Due to slow nail growth, the treatment takes 3-9 months depending on the nail size and infected area. H...

Development of ciclopirox olamine topical formulations: evaluation of drug release, penetration and cutaneous retention.

Pharm. Dev. Technol. 20(2) , 197-203, (2015)

With the aim of reducing system absorption and consequently, the side effects, and simultaneously select a penetration enhancing, three topical formulations with 0.5% ciclopirox olamine (CO) and 15% o...

The low keratin affinity of efinaconazole contributes to its nail penetration and fungicidal activity in topical onychomycosis treatment.

Antimicrob. Agents Chemother. 58(7) , 3837-42, (2014)

Onychomycosis is a common fungal nail disease that is difficult to treat topically due to the deep location of the infection under the densely keratinized nail plate. Keratin affinity of topical drugs...