Pivmecillinam hydrochloride

Names

[ Name ]:
Pivmecillinam hydrochloride

[Synonym ]:
2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate,hydrochloride
2-Pyrrolidinecarboxamide,1-(2,2-dimethyl-1-oxopropyl)-N-methyl
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(1E)-(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (2S,5R,6R)-, hydrochloride (1:1)
[(2,2-Dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(E)-(1-azepanylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride (1:1)
Piv-DL-Pro-NHMe

Biological Activity

[Description]:

Pivmecillinam hydrochloride (FL-1039 hydrochloride) is an orally active prodrug of mecillinam, an extended-spectrum penicillin antibiotic.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Nicolle LE. Pivmecillinam in the treatment of urinary tract infections. J Antimicrob Chemother. 2000 Aug;46 Suppl A:35-39.

[2]. Graninger W. Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8.

[3]. Holme E, et al. Carnitine deficiency induced by pivampicillin and pivmecillinam therapy. Lancet. 1989 Aug 26;2(8661):469-73.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3g/cm3

[ Boiling Point ]:
581ºC at 760mmHg

[ Melting Point ]:
172-173°

[ Molecular Formula ]:
C₂₁H₃₄ClN₃O₅S

[ Molecular Weight ]:
476.030

[ Flash Point ]:
305.2ºC

[ Exact Mass ]:
475.190765

[ PSA ]:
113.81000

[ LogP ]:
3.08940

[ Storage condition ]:
-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XI0187000

CHEMICAL NAME :: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1H-azepin-1-yl) methylene)amino)-3,3-dimethyl-7-oxo-, hydroxymethyl ester, pivalate (ester), monohydrochloride, (+)-

CAS REGISTRY NUMBER :: 32887-03-9

LAST UPDATED :: 199509

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C21-H33-N3-O5-S.Cl-H

MOLECULAR WEIGHT :: 476.09

WISWESSER LINE NOTATION :: T45 ANV ESTJ GVO1OVX1&1&1 CNU1- AT7NTJ &GH

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 :: 9500 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: 6,632,1982

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2100 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: 9,1066,1978

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 465 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: 9,1066,1978

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3020 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: 6,632,1982

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1930 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: 9,1066,1978

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 475 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: 9,1066,1978 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 115 gm/kg/26W-I

TOXIC EFFECTS :: 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: 11,46,1977 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 57330 mg/kg

SEX/DURATION :: male 91 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 2,171,1976

Related Compounds

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