6-Aminopenicillansure
6-Aminopenicillanic acid
Grundinformationen
- CAS
551-16-6- Standard-SMILES
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O- InChIKey
NGHVIOIJCVXTGV-ALEPSDHESA-N- Summenformel
- C8H12N2O3S
- Durchschnittliche Molmasse
- 216,26 g/mol
- Monoisotopische Masse
- 216,05686342
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 acid6-Aminopenicillamine acidPhenacyl 6-aminopenicillinate6-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)
DTXSID7046097QR0C4R7XVN6-amino-2,2-dimethylpenam-3alpha-carboxylic acidCHEBI:167056-APA cpdNSC-500714-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-DTXCID5026097
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -2,1
- Polarare Oberfläche (TPSA)
- 109 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 318
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Metabolite of Penicillin G, Penicillin V
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.
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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 InformationREACH registered substance: 6-aminopenicillanic acid (EC: 208-993-4)
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
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
Zugehörige Reaktionen
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