Clarithromycin 9-Oxime

HCID 9962216

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Basic information

CAS: 103450-87-9
Standard SMILES: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(OC)C[C@@H](C)/C(=N\O)[C@H](C)[C@@H](O)[C@]1(C)O
InChIKey: MWBJRTBANFUBOX-SQYJNGITSA-N
Molecular formula: C38H70N2O13
Average molar mass: 763 g/mol
Monoisotopic mass: 762.48779029

Names & identifiers

Preferred name: Clarithromycin 9-Oxime
IUPAC: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
English name: Clarithromycin (9Z)-Oxime
Molecular formula: C38H70N2O13
Molecular weight: 762.98

Names & synonyms

Clarithromycin 9-Oxime103450-87-9Clarithromycin (9Z)-OximeClarithromycin E-9-OximeClarithromycin 9-Oxime (E/Z mixture)127253-06-9(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one127253-05-8Clarithromycin EP impurity C6-O-Methylerythromycin A (E)-9-oxime; Oxacyclotetradecane, erythromycin deriv.; 9(E)-6-O-Methyl-erythromycin oximeErythromycin, 6-O-methyl-, 9-oxime, (9Z)-WWW97Q57W2

Show more names

CLARITHROMYCIN Z-OXIME6-O-methyl Ery A 9(Z)-oximeClarithromycin EP Impurity LClarithromycin Impurity L(EP)Clarithromycin EP Impurity L (USP RC L)Clarithromycin related compound L, EvoPureClarithromycin Impurity 12(Clarithromycin EP Impurity L)

CHEMBL4277273SCHEMBL25926088DTXSID20433331(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-10-(hydroxyimino)-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,Z)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-10-(hydroxyimino)-7-methoxy-6-O-Methylerythromycin A (Z)-9-oximeG91064(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy-10-(hydroxyimino)-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one

Database identifiers

CAS: 103450-87-9、127253-05-8
PubChem CID: 9962216
DTXSID: DTXSID20433331
ChEMBL: CHEMBL4277273
UNII: WWW97Q57W2

Properties

Computed structural properties

XLogP: 3.4
Topological polar surface area: 198 Å²
Hydrogen bond donors: 5
Hydrogen bond acceptors: 15
Rotatable bonds: 8
Heavy atoms: 53
Formal charge: 0
Complexity: 1,230

Physicochemical properties

Melting point: 212 · 212-215oC
Boiling point: 827.7 · 827.7±65.0 °C(Predicted)
Density: 1.26 · 1.26±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C Freezer, Under inert atmosphere
solubility: Chloroform (Slightly), Methanol (Slightly)
pka: 11.94 · 11.94±0.70(Predicted)
form: Solid
color: White to Off-White
Major Application: pharmaceutical small molecule
InChIKey: MWBJRTBANFUBOX-YFKXTQMRNA-N
UNSPSC Code: 12352200 · 12352200
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07,GHS09
Signal word: Warning
Hazard statements: 302 · H302-H410
Precautionary statements: 264 · P264-P270-P273-P301+P312-P391-P501
WGK Germany: 3 · WGK 3
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1

Safety & regulation

Safety data

wgk: WGK 3
Signal word: Warning
Symbol(GHS): GHS07,GHS09
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H410
Hazard Classifications: Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
Precautionary statements: P264-P270-P273-P301+P312-P391-P501

Chemistry & industry

Applications

UsesClarithromycin (9Z)-Oxime (Clarithromycin EP Impurity L) is an impurity of Clarithromycin (C559750); a semi-synthetic macrolide antibiotic and derivative of Erythromycin (E650000).