Penamecillin: Difference between revisions

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+{{Short description|Chemical compound}}
-{{Wikify|date=September 2011}}
+{{cs1 config|name-list-style=vanc|display-authors=6}}
 {{Drugbox
+| Verifiedfields = changed
 | Watchedfields = changed
-| verifiedrevid = 443295344
+| verifiedrevid = 448868650
 | IUPAC_name = (acetyloxy)methyl (2''S'',5''R'',6''R'')-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
-| image = Penamecillin.png
+| image = Penamecillin.svg
 <!--Clinical data-->
 | tradename =
 | Drugs.com = {{drugs.com|international|penamecillin}}
 | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
 | pregnancy_US = <!-- A / B            / C / D / X -->
 | pregnancy_category =
 | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
 | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
 | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
 | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
 | legal_status =
 | routes_of_administration =
 <!--Pharmacokinetic data-->
 | bioavailability =
 | protein_bound =
 | metabolism =
 | elimination_half-life =
 | excretion =
 <!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 983-85-7
 | ATC_prefix = J01
@@ Line 33: / Line 35: @@
 | PubChem = 13795
 | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank =
 | UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = H0P1YE5581
+| ChEBI_Ref = {{ebicite|changed|EBI}}
+| ChEBI = 131733
 | KEGG_Ref = {{keggcite|correct|kegg}}
 | KEGG = D05406
+| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
+| ChemSpiderID      = 8426255
 <!--Chemical data-->
 | C=19 | H=22 | N=2 | O=6 | S=1
+| smiles            = CC(=O)OCOC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)(C)C
-| molecular_weight = 406.45278
+| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChI          = 1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1
+| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChIKey       = NLOOMWLTUVBWAW-HLLBOEOZSA-N
 }}
-'''Penamecillin''', a acetoxymethyl ester of benzylpenicillin, is a [[Prodrug|pro-drug]] that is processed to benzylpenicillin by esterases.<ref>{{cite journal |author=Agersborg HPK |title=THE PHARMACOLOGY OF PENAMECILLIN |journal=Brit. J. Pharmacol. |volume=26 |issue=3 |pages=649–55 |year=1966 |pmid= 4959939|doi= |last2=Batchelor |first2=A |last3=Cambridge |first3=GW |last4=Rule |first4=AW |pmc=1510697}}</ref>
+'''Penamecillin''', an acetoxymethyl ester of benzylpenicillin, is a [[prodrug]] processed to [[benzylpenicillin]] by esterases.<ref>{{cite journal | vauthors = Agersborg HP, Batchelor A, Cambridge GW, Rule AW | title = The pharmacology of penamecillin | journal = British Journal of Pharmacology and Chemotherapy | volume = 26 | issue = 3 | pages = 649–655 | date = March 1966 | pmid = 4959939 | pmc = 1510697 | doi = 10.1111/j.1476-5381.1966.tb01844.x }}</ref> It has no detectable teratogenic risk to the fetus.<ref>{{cite journal | vauthors = Czeizel AE, Rockenbauer M, Sørensen HT, Olsen J | title=The Safety of Penicillin V: Oral Penamecillin Use During Pregnancy The Importance and Limitation of Recall Bias | journal=Congenital Anomalies | volume=39 | issue=4 | date=1999 | issn=0914-3505 | doi=10.1111/j.1741-4520.1999.tb00566.x | pages=267–279}}</ref>
-==References==
+== References ==
-{{Reflist|1}}
+{{Reflist}}
 {{Cell wall disruptive antibiotics}}
-[[Category:Beta-lactam antibiotics]]
+[[Category:Penicillins]]
 {{antibiotic-stub}}