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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Pivmecilinamo clorhidrato, Chebi:51213, Schembl1650614, [(2,2-dimethylpropanoyl)oxy]methyl 6beta-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3alpha-carboxylate hydrochloride, 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;hydron;chloride

Molecular Formula

C₂₁H₃₄ClN₃O₅S

Molecular Weight

476.0 g/mol

InChI Key

UHPXMYLONAGUPC-WKLLBTDKSA-N

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.

1 2D Structure

Pivmecilinamo Clorhidrato

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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;hydron;chloride

2.1.2 InChI

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/t14-,15+,17-;/m1./s1

2.1.3 InChI Key

UHPXMYLONAGUPC-WKLLBTDKSA-N

2.1.4 Canonical SMILES

[H+].CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C.[Cl-]

2.1.5 Isomeric SMILES

[H+].CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C.[Cl-]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Amdinocillin Pivoxil

2. Fl 1039

3. Fl-1039

4. Fl1039

5. Hydrochloride, Pivmecillinam

6. Mecillinam Pivaloyl Ester

7. Pivaloyl Ester, Mecillinam

8. Pivamdinocillin

9. Pivmecillinam

10. Pivmecillinam Hydrochloride

11. Pivoxil, Amdinocillin

2.2.2 Depositor-Supplied Synonyms

1. Pivmecilinamo Clorhidrato

2. Chebi:51213

3. Schembl1650614

4. [(2,2-dimethylpropanoyl)oxy]methyl 6beta-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3alpha-carboxylate Hydrochloride

5. 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;hydron;chloride

2.3 Create Date

2009-01-30

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₄ClN₃O₅S
Molecular Weight	476.0 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	8
Exact Mass	475.1907701 g/mol
Monoisotopic Mass	475.1907701 g/mol
Topological Polar Surface Area	114 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	710
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Anti-Infective Agents, Urinary

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

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