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Pivmecillinam

Pivmecillinam structure

CAS No:
32886-97-8
Formula:
C21H33N3O5S
Chemical Name:
Pivmecillinam
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-,(2,2-dimethyl-1-oxopropoxy)methyl ester,(2S,5R,6R)-;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),(+)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-,(2,2-dimethyl-1-oxopropoxy)methyl ester,[2S-(2α,5α,6β)]-;FL 1039;Pivmecillinam;Amdinocillin pivoxil;Pivamdinocillin
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

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

Solid

Pivmecillinam is a penicillanic acid ester that is the [(2,2-dimethylpropanoyl)oxy]methyl ester and prodrug of mecillinam. It has a role as an antiinfective agent, an antibacterial drug and a prodrug. It is a penicillanic acid ester, a penicillin and a pivaloyloxymethyl ester. It derives from a mecillinam.|Amdinocillin Pivoxil is the pivoxil ester form of a semisynthetic, broad spectrum beta-lactam penicillin with antibacterial activity. Amdinocillin specifically binds to and inactivates penicillin-binding protein 2 (PBP 2) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis.|Pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin.

Pivmecillinam Basic Attributes

Molecular Weight：

439.57

Exact Mass：

439.57

EC Number：

251-276-6

UNII：

1WAM1OQ30B

DSSTox ID：

DTXSID7048538

NCI Thesaurus Code：

C76216

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

114

XLogP3：

2.97

Appearance：

white to beige

Density：

1.3±0.1 g/cm3

Melting Point：

119 °C

Boiling Point：

581.0±60.0 °C at 760 mmHg

Flash Point：

305.2±32.9 °C

Refractive Index：

1.604

Water Solubility：

DMSO: soluble 5mg/mL, clear (warmed)

Storage Conditions：

-20°C

Toxicity：

LD50 in mice, rats (mg/kg): 475-480, 465 i.v.; 1736-1930, 1935-2100 s.c.; 3020, 9500-10000 orally (Sato)

Specific rotation：

D20 +231° (c = 1 in 96% ethanol)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-37/39

RTECS Number：

XI0185000

Marks：

Drug Information

Drug Indication：

Used to treat infections due to mecillinam-sensitive organisms such as urinary tract infections, salmonellosis and typhoid fever.

Pharmacology：

Pivmecillinam is a pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

Absorption：

Well absorbed following oral administration.

Mechanism of Action：

Pivmecillinam interferes with the biosynthesis of the bacterial cell wall however its activity is slightly different from that of other penicillins and cephalosporins

MeSH Entry Terms：

Amdinocillin Pivoxil

Pivmecillinam Use and Manufacturing

Antibacterial.

Computed Properties

Molecular Weight:439.6
XLogP3:3.1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:8
Exact Mass:439.21409234
Monoisotopic Mass:439.21409234
Topological Polar Surface Area:114
Heavy Atom Count:30
Complexity:710
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Pivmecillinam

Shaanxi Dideu Medichem Co. Ltd Contact Supplier

CN
5 YRS

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Pivmecillinam 32886-97-8 99%

CAS No.: 32886-97-8

Grade: Industrial Grade

Content: 98%

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