6-Aminopenicillanic acid (HCID 11082)

Überblick

6-aminopenicillanic acid is a penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and pharmacologic characteristics. It has a role as an allergen. It is functionally related to a penicillanic acid. It is a conjugate acid of a 6-aminopenicillanate. It is a tautomer of a 6-aminopenicillanic acid zwitterion.

Namen und Bezeichner

Bevorzugter Name: 6-Aminopenicillanic acid
IUPAC: (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Lokaler Name: 6-Aminopenicillansure
Englischer Name: 6-Aminopenicillanic acid
Summenformel: C8H12N2O3S
Molmasse: 216.26

Namen und Synonyme

6-Aminopenicillanic acid551-16-66-ApaPenicinPenin6-ApsAminopenicillanic acid(+)-6-Aminopenicillanic acid(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidPhenacyl 6-aminopenicillinate6-Aminopenicillamine acid6-aminopenicillanate

Weitere Namen anzeigen

Amoxicillin EP Impurity AAMoxicillin Related CoMpound A6-amino penicillanic acid(6-APA)6-AminoFlucloxacillin EP Impurity C6-AMINO-2,2-DIMETHYL-5-OXOPERHYDROAZETO[2,1-B][1,3]THIAZOLE-3-CARBOXYLIC ACID6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACIDAmoxicillin Related Compound A (15 mg) ((2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

DTXSID7046097QR0C4R7XVNCHEBI:16705NSC-500716-amino-2,2-dimethylpenam-3alpha-carboxylic acid4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-DTXCID5026097CHEBI:30938

Datenbank-Bezeichner

CAS: 551-16-6
PubChem CID: 11082
DTXSID: DTXSID7046097
ChEMBL: CHEMBL1236749
ChEBI: CHEBI:16705
UNII: QR0C4R7XVN
EC Number: 208-993-4
Nikkaji: J14.224G

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -2,1
Polarare Oberfläche (TPSA): 109 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 1
Schwere Atome: 14
Formalladung: 0
Komplexität: 318

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Metabolite of Penicillin G, Penicillin V

Pharmaceuticals -> Antibiotics

Dissociation Constants2.3

Physikochemische Eigenschaften

Schmelzpunkt: 198 · 198-200 °C (dec.)(lit.)
Siedepunkt: 460.2 · 460.2±45.0 °C(Predicted)
Dichte: 1.3418 · 1.3418 (rough estimate)
Brechungsindex: 1.63 · 1.6300 (estimate)
storage temp.: 2 · 2-8°C
Löslichkeit: 2.46 g/l · 2.46g/l
pka: 2.3 · pKa 2.3 (Uncertain)
Aggregatzustand: Fine Powder
Farbe: White to cream
PH: 3.4 · 3.4 (100g/l, H2O)
Wasserlöslichkeit: Soluble in water and hydrochoric acid.
Merck: 14 · 14,458
BRN: 15080 · 15080
Stabilität: Light sensitive
InChI: 1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
InChIKey: NGHVIOIJCVXTGV-SDKNWNMFSA-N
SMILES: CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O
LogP: -3.87 at · -3.87 at 22.5℃
CAS Datenbank: 551 · 551-16-6(CAS DataBase Reference)
EPA chemische Informationen: 6 · 6-Aminopenicillanic acid (551-16-6)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 79.4% (50 of 63) of all reports.

Danger

H317 (15.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 63 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 17-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/14138

Hazard Classes and CategoriesSkin Sens. 1 (15.9%)

Sicherheitsdaten

F: 10
wgk: 2
tsca: TSCA listed
hs_code: 29349990
RTECS-Nr.: XH8225000
risk_code: 42/43
hazard_code: Xn
safety_code: 22-36/37-45-37-24-36
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Eye Irrit. 2

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsKidney

Cellular LocationsCytoplasm

Verwendung und Herstellung

General Manufacturing Information4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-: INACTIVE

Anwendungen · 1 Eintrag

Verwenden(+)-6-Aminopenicillanic Acid is the core structure in penicillins, obtained from the fermentation brew of the Penicillium mold. (+)-6-Aminopenicillanic Acid is used as the main starting block for the preparation of numerous semisynthetic penicillins.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Nachgelagerte Produkte

[2S-[2α,5α,6β(S*)]]-6-[[[[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carbonsure Carbenicillin 6-(2-Phenylacetamido)penicillansure Primaxin monohydrate Oxacillin sodium monohydrate Natrium-[2S-(2α,5α,6β)]-6-[[[3-(2-chlor-6-fluorphenyl)-5-methylisoxazol-4-yl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carboxylat [2S-(2α,5α,6α)]-6-Brom-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carbonsure (2S-cis)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carbonsure (3S)-6,6-Dibromo-2,2-dimethylpenam-3-carboxylic acid 1,1-dioxide Meticillin 4-Thiazolecarboxylic acid 6β-Phthalimidopenicillanic Acid

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and ph rmacologic characteristics.

Zugehörige Reaktionen

65

Reaktionsaufzeichnung erstellen

HRID 64994als Produktuspto-grants-1986_09

HRID 127997als Produktuspto-grants-1981_03

HRID 128504als Eduktuspto-grants-1995_11

HRID 267182als Produktuspto-grants-1976_03

HRID 267183als Produktuspto-grants-1976_03

HRID 267184als Produktuspto-grants-1976_03

HRID 329240als Eduktuspto-grants-1977_04

HRID 364727als Eduktuspto-grants-1986_08

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