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Drug Details

General Information of the Drug (ID: DR2755)
Name
Penicillin G
Synonyms
penicillin g; Benzylpenicillin; Benzylpenicillinic acid; Free penicillin II; Pfizerpen; Benzyl penicillin; Bencilpenicilina; Benzylpenicillinum; 61-33-6; Benzylpenicilline; Benzylpenicillin G; 6-(2-Phenylacetamido)penicillanic acid; Free penicillin G; Benzopenicillin; Dropcillin; Gelacillin; Liquacillin; Pharmacillin; Cilopen; Pradupen; Specilline G; Benzylpenicillin potassium; (5R,6R)-Benzylpenicillin; Penicillin, (phenylmethyl)-; Galofak; Free benzylpenicillin; Penicillin-G potassium; Compocillin G; bensylpenicillin; benzyl benicillin; Pfizerpen-AS; Penicillinic acid, (phenylmethyl)-; Phenylacetamidopenicillanic acid; Pencillin G; UNII-Q42T66VG0C; Cilloral; Cosmopen; PENICILLIN-2; CHEBI:18208; Benzyl-6-aminopenicillinic acid; Penicillinic acid, benzyl-; (Phenylmethyl)penicillin; Q42T66VG0C; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Ursopen; (Phenylmethyl)penicillinic acid; 61-33-6 (FREE ACID); (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)- (2S-(2alpha,5alpha,6beta))-; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-; Cillora; PenicillinG; Bencilpenicilina [Spanish]; Benzylpenicilline [French]; Benzylpenicillinum [Latin]; Benzylpenicillin [INN:BAN]; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- [2S-(2alpha,5alpha,6beta)]-; PNN; SMR000538912; HSDB 3166; EINECS 200-506-3; NSC 193396; BRN 0044740; NSC-193396; J01CE01; Penicillin,(S); 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-; PENICILLIN-G; Spectrum_000933; Benzylpenicillin (INN); CHEMBL29; Prestwick0_001078; Prestwick1_001078; Prestwick2_001078; Prestwick3_001078; Spectrum2_000518; Spectrum3_000542; Spectrum4_000471; Spectrum5_001108; Epitope ID:114070; SCHEMBL3783; BSPBio_001096; BSPBio_002183; KBioGR_000942; KBioSS_001413; 4-27-00-05861 (Beilstein Handbook Reference); 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-, (2S-(2alpha,5alpha,6beta))-; MLS000766897; MLS001032123; MLS001173382; DivK1c_000316; SPBio_000475; SPBio_002998; BPBio1_001206; GTPL4796; DTXSID5046934; KBio1_000316; KBio2_001413; KBio2_003981; KBio2_006549; KBio3_001683; NINDS_000316; HMS2875L09; ZINC3871701; BDBM50022787; Phenylacetyl-6-aminopenicillanic acid; AKOS005203091; DB01053; IDI1_000316; NCGC00159348-02; NCGC00159348-03; (2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-[(PHENYLACETYL)AMINO]-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6- (2-phenylacetamido)-; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-; SBI-0051476.P003; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-; Bicillin (*Benzathine Salt, Tetrahydrate*); C05551; D02336; (2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]; 061P336; Q258450; W-109262; BRD-K55191674-236-03-7; BRD-K55191674-237-02-7; BRD-K55191674-237-12-6; Benzylpenicillin, Antibiotic for Culture Media Use Only; 2,2-dimethyl-6beta-(phenylacetamido)penam-3alpha-carboxylic acid; (+)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid(penicillin G); (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; 3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; 3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid anion (Penicillin G); 3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid(penicillin G); 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)- (8CI); 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-, (2S,5R,6R)-
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Molecular Type
Small molecule
Disease Syphilis [ICD-11: 1A60-1A62] Phase 4 [1]
Structure
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2D MOL

3D MOL

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Formula
C16H18N2O4S
PubChem CID
5904
Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
InChI
1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
InChIKey
JGSARLDLIJGVTE-MBNYWOFBSA-N
CAS Number
CAS 61-33-6
ChEBI ID
CHEBI:18208
TTD Drug ID
D00QAR
DrugBank ID
DB01053
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Bovine lactoferrin      Milk vetch dwarf China alphasatellite     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Nineteen late-lactating cows had all 4 mammary quarters individually inoculated (185 cfu) through the teat cistern with the PG-resistant Staph. Aureus SHY97-4320.
                    Experimental
                    Result(s)
BLF added to PG is an effective combination (i.e., 3- to 5-times higher cure rate) for the treatment of stable Staph. aureu infections highly resistant to beta-lactam antibiotics.
Target and Pathway
Target(s) Bacterial penicillin binding 1 (Bact pbp)  Molecule Info  [3]
Bacterial Penicillin binding protein 3 (Bact mrcA)  Molecule Info  [4]
References
Reference 1 ClinicalTrials.gov (NCT03637660) Phase 4 Comparative Trial of Benzathine Penicillin G for Treatment of Early Syphilis in Subjects With or Without HIV Infection
Reference 2 Efficacy of a lactoferrin-penicillin combination to treat {beta}-lactam-resistant Staphylococcus aureus mastitis. J Dairy Sci. 2007 Jun;90(6):2778-87.
Reference 3 Overexpression, purification and biochemical characterization of a class A high-molecular-mass penicillin-binding protein (PBP), PBP1* and its soluble derivative from Mycobacterium tuberculosis. Biochem J. 2002 Feb 1;361(Pt 3):635-9.
Reference 4 Association of amino acid substitutions in penicillin-binding protein 3 with beta-lactam resistance in beta-lactamase-negative ampicillin-resistant Haemophilus influenzae. Antimicrob Agents Chemother. 2001 Jun;45(6):1693-9.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China