Cas no 32887-03-9 (Pivmecillinam hydrochloride)

Pivmecillinam hydrochloride is a prodrug of mecillinam, an antibiotic belonging to the penicillin class. It is specifically active against Gram-negative bacteria, including many Enterobacteriaceae such as Escherichia coli and Proteus species. The hydrochloride salt form enhances solubility and bioavailability, facilitating oral administration. Pivmecillinam hydrochloride is hydrolyzed in vivo to release the active mecillinam, which inhibits bacterial cell wall synthesis by binding to penicillin-binding protein 2 (PBP-2). Its narrow-spectrum activity minimizes disruption to the normal microbiota, reducing the risk of secondary infections. This compound is particularly valued for its efficacy in treating uncomplicated urinary tract infections (UTIs) and its low propensity for inducing resistance compared to broader-spectrum antibiotics.

Pivmecillinam hydrochloride structure

Product Name:Pivmecillinam hydrochloride

CAS No:32887-03-9

MF:C₂₁H₃₄ClN₃O₅S

MW:476.029763698578

CID:312613

PubChem ID:115162

Update Time:2025-10-29

Pivmecillinam hydrochloride Chemical and Physical Properties

Names and Identifiers

- 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-,(2,2-dimethyl-1-oxopropoxy)methyl ester, hydrochloride (1:1), (2S,5R,6R)-
- 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
- 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-,(2,2-d
- Amdinocillin pivoxil hydrochloride
- PIVMECILLINAM
- Pivmecillinam Hydroc
- pivmecillinam hydrochloride
- 2-Pyrrolidinecarboxamide,1-(2,2-dimethyl-1-oxopropyl)-N-methyl
- Piv-DL-Pro-NHMe
- Melysin
- Selexid
- 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, monohydrochloride, [2S-(2alpha,5alpha,
- s5473
- 48FX7N21H2
- 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, monohydrochloride, [2S-(2alpha,5alpha,6beta)]-
- FL-1039
- DTXCID9025453
- HY-B0810A
- PIVMECILLINAM HYDROCHLORIDE [EP MONOGRAPH]
- Pivmecillinam (hydrochloride)
- HYDROXYMETHYL (2S,5R,6R)-6-(((HEXAHYDRO-1H-AZEPIN-1-YL)METHYLENE)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE PIVALATE (ESTER) HYDROCHLORIDE
- CAS-32887-03-9
- D01499
- CHEMBL4303519
- DTXSID1045453
- Pivmecillinam HCl
- Melysin (TN)
- SR-01000838842-3
- Q27104782
- A913043
- PIVMECILLINAM HYDROCHLORIDE [WHO-DD]
- BS-17014
- 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
- 1H-AZEPIN-1-YL)METHYLENE)AMINO)-3,3-DIMETHYL-7-OXO-, HYDROXYMETHYL ESTER PIVALATE (ESTER), MONOHYDROCHLORIDE, (+)-
- J-018915
- AKOS030526136
- 32887-03-9
- CCG-221053
- pivmecilinamo clorhidrato
- SR-01000838842
- Tox21_110625
- 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, monohydrochloride, (2S-(2alpha,5alpha,6beta))-
- BCP07839
- MLS002154128
- SMR001233435
- CHEBI:51213
- (pivaloyloxy)methyl (2S,5R,6R)-6-(((E)-azepan-1-ylmethylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride
- CHEMBL1355196
- C74675
- Pivmecilinamo clorhidrato [Spanish]
- (Pivaloyloxy)methyl (2S,5R,6R)-6-((azepan-1-ylmethylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride
- PIVMECILLINAM HYDROCHLORIDE [MART.]
- HMS1571C08
- 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, monohydrochloride, (2S,5R,6R)-
- NCGC00016813-01
- Pivmecillinam hydrochloride [JAN]
- AMDINOCILLIN PIVOXIL HYDROCHLORIDE [MI]
- pivmecillinamhydrochloride
- SCHEMBL232687
- Pivmecillinam hydrochloride (JP17)
- EINECS 251-278-7
- Methylene 2,2-dimethylpropanoate (2S,5R,6R)-6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride
- UNII-48FX7N21H2
- FL-1039 hydrochloride
- GLXC-27953
- DA-56908
- PIVYA
- Pivmecillinam hydrochloride (JP18/USAN)
- Pivmecillinam hydrochloride
- Inchi： 1S/C21H33N3O5S.ClH/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23;/h12,14-15,17H,6-11,13H2,1-5H3;1H/b22-12+;/t14-,15+,17-;/m1./s1
- InChI Key： UHPXMYLONAGUPC-YKBWBZKYSA-N
- SMILES： Cl.S1C(C)(C)[C@H](C(=O)OCOC(C(C)(C)C)=O)N2C([C@H]([C@@H]12)/N=C/N1CCCCCC1)=O

Computed Properties

Exact Mass: 475.19100
Monoisotopic Mass: 475.1907701g/mol
Isotope Atom Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 8
Heavy Atom Count: 31
Rotatable Bond Count: 8
Complexity: 710
Covalently-Bonded Unit Count: 2
Defined Atom Stereocenter Count: 3
Undefined Atom Stereocenter Count : 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Topological Polar Surface Area: 114?2

Experimental Properties

Melting Point: 172-173°
Boiling Point: 581°C at 760 mmHg
PSA: 113.81000
LogP: 3.08940
Specific Rotation: D20 +219° (c = 1 in 0.1N HCl)

Pivmecillinam hydrochloride Security Information

Signal Word：Warning
Hazard Statement： H302-H315-H319-H335
Warning Statement： P261-P305+P351+P338
Storage Condition：Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month

Pivmecillinam hydrochloride Pricemore >>

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S e l l e c k ZHONG GUO	S5473-25mg	Pivmecillinam hydrochloride	32887-03-9	99.04%	25mg	￥1040.47	2023-12-06
ChemScence	CS-4222-10mg	Pivmecillinam hydrochloride	32887-03-9	≥98.0%	10mg	$60.0	2022-04-27
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SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd.	P873622-5mg	Pivmecillinam hydrochloride	32887-03-9	99%	5mg	￥434.70	2022-01-14
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Pivmecillinam hydrochloride Suppliers

Amadis Chemical Company Limited

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(CAS:32887-03-9)Pivmecillinam hydrochloride

Order Number:A913043

Stock Status:in Stock

Quantity:250mg/1g

Purity:99%

Pricing Information Last Updated:Friday, 30 August 2024 12:47

Price ($):164.0/223.0

Email:[email protected]

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Additional information on Pivmecillinam hydrochloride

Comprehensive Overview of Pivmecillinam Hydrochloride (CAS No. 32887-03-9): Mechanism, Applications, and Modern Relevance

Pivmecillinam hydrochloride (CAS No. 32887-03-9), a prodrug of mecillinam, is a beta-lactam antibiotic belonging to the penicillin class. Its unique chemical structure and mechanism of action make it a critical therapeutic agent, particularly for treating urinary tract infections (UTIs) caused by Gram-negative bacteria. The compound's prodrug form, pivmecillinam, enhances oral bioavailability, allowing for effective systemic delivery. This article explores its pharmacology, clinical applications, and relevance in the era of antibiotic resistance—a pressing global health concern.

The rise of antimicrobial resistance (AMR) has intensified the search for antibiotics like pivmecillinam hydrochloride that retain efficacy against resistant strains. Studies highlight its activity against Escherichia coli and Klebsiella pneumoniae, common UTI pathogens. Unlike traditional penicillins, mecillinam targets penicillin-binding protein 2 (PBP2), disrupting cell wall synthesis in a distinct manner. This specificity reduces cross-resistance risks, making it a valuable tool in antibiotic stewardship programs.

From a chemical perspective, CAS No. 32887-03-9 refers to the hydrochloride salt of pivmecillinam, which hydrolyzes to mecillinam in vivo. The pivaloyloxymethyl ester group in its structure improves lipophilicity, facilitating intestinal absorption. This pharmacokinetic advantage is a focal point for researchers optimizing oral antibiotic formulations. Recent trends in drug delivery systems and personalized medicine further underscore its significance.

Clinically, pivmecillinam hydrochloride is first-line therapy for uncomplicated UTIs in regions like Scandinavia, where resistance rates remain low. Its targeted spectrum minimizes disruption to gut microbiota—a growing priority in microbiome health discussions. Patients and healthcare providers frequently search for "pivmecillinam vs. nitrofurantoin" or "pivmecillinam side effects", reflecting demand for comparative efficacy data. Rigorous clinical trials confirm its safety profile, with gastrointestinal disturbances being the most reported adverse effect.

Environmental and synthetic considerations also arise. The synthesis of CAS 32887-03-9 involves protecting group chemistry to stabilize the beta-lactam ring. Green chemistry initiatives aim to reduce waste in its production, aligning with sustainable pharmaceutical manufacturing goals. Analytical methods like HPLC and LC-MS ensure quality control, addressing concerns about drug purity—a hot topic in pharmacovigilance forums.

In summary, pivmecillinam hydrochloride exemplifies how classic antibiotics adapt to modern challenges. Its niche targeting of Gram-negative bacteria, coupled with prodrug innovation, offers lessons for future anti-infective drug development. As AMR escalates, compounds like CAS No. 32887-03-9 will remain pivotal in bridging therapeutic gaps while researchers pursue next-generation solutions.

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