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    Chemistry

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    Also known as: Cefalexin, 15686-71-2, Cephacillin, Keflex, Ceporexin, Cepexin
    Molecular Formula
    C16H17N3O4S
    Molecular Weight
    347.4  g/mol
    InChI Key
    ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
    FDA UNII
    5SFF1W6677
    Cephalexin
    A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of CEPHALORIDINE or CEPHALOTHIN, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms.
    Cephalexin anhydrous is a Cephalosporin Antibacterial.
    1 2D Structure

    Cephalexin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
    2.1.3 InChI Key
    ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
    2.1.4 Canonical SMILES
    CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)N)SC1)C(=O)O
    2.1.5 Isomeric SMILES
    CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)SC1)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    5SFF1W6677
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((aminophenylacetyl)amino)-3-methyl-8-oxo-, (6r-(6alpha,7beta(r*)))-

    2. Cefalexin

    3. Cephalexin Dihydride

    4. Cephalexin Hemihydrate

    5. Cephalexin Hydrochloride

    6. Cephalexin Monohydrate

    7. Cephalexin Monohydrochloride

    8. Cephalexin Monohydrochloride, Monohydrate

    9. Cephalexin, (6r-(6alpha,7alpha(r*)))-isomer

    10. Cephalexin, (6r-(6alpha,7beta(s*)))-isomer

    11. Cephalexin, (6r-(6alpha,7beta))-isomer

    12. Cephalexin, Monosodium Salt

    13. Cephalexin, Monosodium Salt, (6r-(6alpha,7beta))-isomer

    14. Ceporexine

    15. Palitrex

    2.3.2 Depositor-Supplied Synonyms

    1. Cefalexin

    2. 15686-71-2

    3. Cephacillin

    4. Keflex

    5. Ceporexin

    6. Cepexin

    7. Cephalexinum

    8. Cepastar

    9. Cephalexine

    10. Celexin

    11. Ceporex

    12. Alcephin

    13. Alsporin

    14. Carnosporin

    15. Cefablan

    16. Cefaleksin

    17. Cefalexina

    18. Cefalexine

    19. Cefalexinum

    20. Durantel

    21. Mamalexin

    22. Sinthecillin

    23. Uphalexin

    24. Cefadin

    25. Felexin

    26. Pyassan

    27. Tepaxin

    28. Keflet

    29. Palitrex

    30. Cefalessina [dcit]

    31. Cephalexin Anhydrous

    32. Cefaseptin

    33. Novolexin

    34. Biocef

    35. Keftab

    36. Cefalexine [inn-french]

    37. Cefalexinum [inn-latin]

    38. Cefalexina [inn-spanish]

    39. Panixine Disperdose

    40. Lilly 66873

    41. 7-(d-alpha-aminophenylacetamido)desacetoxycephalosporanic Acid

    42. Ceporexine

    43. Cefalexin Anhydrous

    44. Cefalexin [inn]

    45. Anhydrous Cephalexin

    46. Ceffanex

    47. Cephanasten

    48. 7-beta-(d-alpha-amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic Acid

    49. Cefaloto

    50. Ceforal

    51. Chebi:3534

    52. Cophalexin

    53. Factagard

    54. Kefalospes

    55. Lexibiotico

    56. Lopilexin

    57. Neolexina

    58. Ortisporina

    59. Sartosona

    60. Sencephalin

    61. Servispor

    62. Tokiolexin

    63. Cefadal

    64. Cefadina

    65. Cefalin

    66. Cefovit

    67. Cephaxin

    68. Erocetin

    69. Ibrexin

    70. Inphalex

    71. Kefolan

    72. Kekrinal

    73. Kidolex

    74. Lafarine

    75. Larixin

    76. Lenocef

    77. Lonflex

    78. Madlexin

    79. Mamlexin

    80. Medoxine

    81. Oriphex

    82. Ospexin

    83. Pectril

    84. Sanaxin

    85. Sepexin

    86. Sialexin

    87. Sporicef

    88. Sporidex

    89. Zozarine

    90. Alexin

    91. Cefax

    92. Cephin

    93. Cepol

    94. Check

    95. Fexin

    96. Ibilex

    97. Neokef

    98. Nufex

    99. Oracef

    100. Oroxin

    101. Roceph

    102. Syncl

    103. Syncle

    104. Synecl

    105. Voxxim

    106. Winlex

    107. Cex

    108. Cefa-iskia

    109. Ceporex Forte

    110. Ceporexin-e

    111. Sq 20248

    112. Chembl1727

    113. Durantel Ds

    114. L-keflex

    115. (6r,7r)-7-{[(2r)-2-amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    116. Cefalessina

    117. Ed A-ceph

    118. Roceph Distab

    119. 5sff1w6677

    120. Ncgc00159522-02

    121. Ceflax

    122. Dsstox_cid_2780

    123. Dsstox_rid_76726

    124. Dsstox_gsid_22780

    125. (6r,7r)-7-((r)-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    126. (6r,7r)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    127. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2r)-aminophenylacetyl]amino]-3-methyl-8-oxo-, (6r,7r)-

    128. L-cephalexin

    129. Cephalexin 1-hydrate

    130. Cerexin

    131. Optocef

    132. Cephalexin [usan:ban]

    133. (6r,7r)-7-[(2r)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    134. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2r)-aminophenylacetyl)amino)-3-methyl-8-oxo-, (6r,7r)-

    135. Smr000338536

    136. S 6437

    137. Cas-15686-71-2

    138. Keflex (tn)

    139. Hsdb 3022

    140. Nsc-758162

    141. Einecs 239-773-6

    142. Brn 0965503

    143. Taicelexin

    144. 7-(d-2-amino-2-phenylacetamido)-3-methyl-delta3-cephem-4-carboxylic Acid

    145. Cerexins

    146. Amplex

    147. Unii-5sff1w6677

    148. Anhydrous Cefalexin

    149. Cefalexin,(s)

    150. (6r,7r)-7-((r)-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    151. 34632-04-7

    152. Cefadros

    153. Cephamasten

    154. Efalexin

    155. Garasin

    156. Iwalexin

    157. Kefloridina

    158. Oracocin

    159. Cefalexin (jp17)

    160. Cephalexin (cefalexin)

    161. Cefalexin [jan]

    162. Cephalexin [mi]

    163. Prestwick0_000358

    164. Prestwick1_000358

    165. Prestwick2_000358

    166. Prestwick3_000358

    167. Cephalexin [hsdb]

    168. Epitope Id:117132

    169. Cefalexin [who-dd]

    170. Schembl2961

    171. 7-(d-2-amino-2-phenylacetamido)-3-methyl-delta (sup 3)-cephem-4- Carboxylic Acid

    172. Bspbio_000455

    173. (6r,7r)-7-((r)-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure

    174. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((aminophenylacetyl)amino)-3-methyl-8-oxo-, (6r-(6alpha,7beta(r*)))-

    175. Mls000759527

    176. Mls001424036

    177. Spbio_002376

    178. Bpbio1_000501

    179. Gtpl4832

    180. Dtxsid9022780

    181. Lilly-66873

    182. Bcpp000289

    183. Hms2051a04

    184. Hy-b0200

    185. Zinc3830500

    186. Tox21_111740

    187. Bdbm50139896

    188. Akos004119846

    189. Tox21_111740_1

    190. Bcp9000509

    191. Ccg-100831

    192. Cs-2137

    193. Db00567

    194. Nc00081

    195. Nsc 758162

    196. Ncgc00159522-03

    197. Ncgc00159522-05

    198. (6r,7r)-7-[[(2r)-2-amino-2-phenyl-acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    199. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(2-amino-2-phenylacetamido)-3-methyl-8-oxo-, D-

    200. Ds-11971

    201. B1692

    202. Cefalexin, Vetranal(tm), Analytical Standard

    203. C-2660

    204. C06895

    205. D00263

    206. H10995

    207. S-6437

    208. Cephalexin, Antibiotic For Culture Media Use Only

    209. Q411417

    210. Q-200819

    211. Brd-k90733503-002-03-6

    212. Cefalexin, British Pharmacopoeia (bp) Reference Standard

    213. Cephalexin Monohydrate, Antibiotic For Culture Media Use Only

    214. Cephalexin, Pharmaceutical Secondary Standard; Certified Reference Material

    215. 7-(d-.alpha.-amino-.alpha.-phenylacetamido)-3-methyl-3-cephem-4-carboxylic Acid

    216. 7beta-[(2r)-2-amino-2-phenylacetamido]-3-methyl-3,4-didehydrocepham-4-carboxylic Acid

    217. (6r,7r)-7-((r)-2-amino-2-phenyl-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    218. (6r,7r)-7-((r)-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    219. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((aminophenylacetyl)amino)-3-methyl-8-oxo-,(6r-(6.alpha.,7.beta.(r*)))-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 347.4 g/mol
    Molecular Formula C16H17N3O4S
    XLogP30.6
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count4
    Exact Mass347.09397721 g/mol
    Monoisotopic Mass347.09397721 g/mol
    Topological Polar Surface Area138 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity600
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameCephalexin
    PubMed HealthCephalexin (By mouth)
    Drug ClassesAntibiotic
    Drug LabelCephalexin, USP is a semisynthetic cephalosporin antibiotic intended for oral administration. It is 7- (D--Amino--phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid monohydrate. Cephalexin has the molecular formula C16H17N3O4S H2O and the m...
    Active IngredientCephalexin
    Dosage FormTablet; Capsule; For suspension
    RouteOral
    Strengtheq 750mg base; eq 250mg base/5ml; eq 500mg base; eq 333mg base; eq 250mg base; eq 125mg base/5ml
    Market StatusPrescription
    CompanyRanbaxy; Sun Pharm Inds (in); Belcher Pharms; Teva; Yung Shin Pharm; Alkem Labs; Aurobindo Pharma; Lupin; Hikma Pharms; Orchid Hlthcare; Hikma

    2 of 4  
    Drug NameKeflex
    PubMed HealthCephalexin (By mouth)
    Drug ClassesAntibiotic
    Drug LabelKeflex Capsules (Cephalexin, USP) is a semisynthetic cephalosporin antibiotic intended for oral administration. It is 7-(D--Amino--phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid monohydrate. Cephalexin has the molecular formula C16H17N3O4...
    Active IngredientCephalexin
    Dosage FormCapsule
    RouteOral
    Strengtheq 750mg base; eq 500mg base; eq 250mg base
    Market StatusPrescription
    CompanyShionogi

    3 of 4  
    Drug NameCephalexin
    PubMed HealthCephalexin (By mouth)
    Drug ClassesAntibiotic
    Drug LabelCephalexin, USP is a semisynthetic cephalosporin antibiotic intended for oral administration. It is 7- (D--Amino--phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid monohydrate. Cephalexin has the molecular formula C16H17N3O4S H2O and the m...
    Active IngredientCephalexin
    Dosage FormTablet; Capsule; For suspension
    RouteOral
    Strengtheq 750mg base; eq 250mg base/5ml; eq 500mg base; eq 333mg base; eq 250mg base; eq 125mg base/5ml
    Market StatusPrescription
    CompanyRanbaxy; Sun Pharm Inds (in); Belcher Pharms; Teva; Yung Shin Pharm; Alkem Labs; Aurobindo Pharma; Lupin; Hikma Pharms; Orchid Hlthcare; Hikma

    4 of 4  
    Drug NameKeflex
    PubMed HealthCephalexin (By mouth)
    Drug ClassesAntibiotic
    Drug LabelKeflex Capsules (Cephalexin, USP) is a semisynthetic cephalosporin antibiotic intended for oral administration. It is 7-(D--Amino--phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid monohydrate. Cephalexin has the molecular formula C16H17N3O4...
    Active IngredientCephalexin
    Dosage FormCapsule
    RouteOral
    Strengtheq 750mg base; eq 500mg base; eq 250mg base
    Market StatusPrescription
    CompanyShionogi

    4.2 Therapeutic Uses

    Cephalosporins

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    /CEPHALEXIN/ HAS ANTIBACTERIAL SPECTRUM SIMILAR TO THAT OF PENICILLINS... AGAINST COCCI & GRAM-POSITIVE BACILLI, PENICILLIN G IS USUALLY MORE EFFECTIVE. ...MOST PENICILLINASES DO NOT AFFECT CEPHALEXIN...

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1119

    ...CEPHALOSPORINS ARE HIGHLY EFFECTIVE IN THERAPY OF VARIETY OF MILD-TO-SEVERE INFECTIONS DUE TO BOTH GRAM-POSITIVE & GRAM-NEGATIVE MICROORGANISMS. /CEPHALOSPORINS/

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1088

    ...CEPHALOSPORIN IS...DRUG OF 1ST CHOICE...FOR KLEBSIELLA INFECTIONS. ... THEY ARE...VALUABLE SECONDARY AGENTS, & THEY FREQUENTLY APPEAR AS ALTERNATIVE CHOICES TO PENICILLIN. /CEPHALOSPORINS/

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1091

    For more Therapeutic Uses (Complete) data for CEPHALEXIN (9 total), please visit the HSDB record page.

    4.3 Drug Warning

    PHYSICIAN MUST ALTER EITHER DRUG DOSAGE OR INTERVAL BETWEEN DOSES WHEN RENAL FUNCTION IS IMPAIRED.

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

    CEPHALOSPORINS SHOULD NOT BE USED TO TREAT BACTERIAL MENINGITIS. THIS IS TRUE FOR ALL CAUSATIVE MICROORGANISMS. ...PENETRATION OF CEPHALOSPORINS INTO CSF IS POOR. /CEPHALOSPORINS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1164

    INFECTIONS DUE TO ENTEROCOCCI ARE USUALLY UNAFFECTED BY THESE CMPD... ENTEROCOCCAL ENDOCARDITIS CANNOT BE CURED WITH CEPHALOSPORIN EVEN WHEN IT IS GIVEN CONCURRENTLY WITH GENTAMICIN OR STREPTOMYCIN. /CEPHALOSPORINS/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1163

    ENTEROBACTER (AEROBACTER) INFECTIONS ARE, AS A RULE, RESISTANT TO THESE CMPD. /CEPHALOSPORINS/

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