Details of the Drug

General Information of Drug (ID: DMVTHER)

• Drug Name: Lincomycin
• Synonyms: Cillimycin; Epilincomycin; Jiemycin; LCM; Lincocin; Lincocine; Lincolcina; Lincolnensin; Lincomicina; Lincomix; Lincomycine; Lincomycinum; Lincomyocin; Lincorex; Mycivin; Lincomycin A; Lincomycine [French]; CBMicro_021584; Lincomix 20; Pura Ject 100; Lincocin (TN); Lincomicina [INN-Spanish]; Lincomycine [INN-French]; Lincomycinum [INN-Latin]; U 10,149A; Lincomycin (USAN/INN); Lincomycin [USAN:INN:BAN]; Lincomycin, (2S-cis)-Isomer; Methyl 6,8-dideoxy-6-[(1-methyl-4-propylprolyl)amino]-1-thiooctopyranoside

Indication

Disease Entry	ICD 11	Status	REF
Gram-positive bacterial infection	1B74-1G40	Approved	[1], [2]

• Therapeutic Class: Antibiotics
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 406.5
  Topological Polar Surface Area (xlogp); 0.2
  Rotatable Bond Count (rotbonds); 7
  Hydrogen Bond Donor Count (hbonddonor); 5
  Hydrogen Bond Acceptor Count (hbondacc); 8
• ADMET Property:
  Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 11.6 mg/L [3]
  Absorption Tmax: The time to maximum plasma concentration (Tmax) is 60 min [3]
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
  Clearance: The clearance of drug is 11.8 +/- 2.4 L/h [5]
  Elimination: Following a 600 mg dose of lincomycin given either intramuscularly or intravenously, the urinary excretion ranges from 1.8-30.3% of the administered dose [3]
  Half-life: The concentration or amount of drug in body reduced by one-half in 5.4 +/- 1.0 hours [3]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 129.942 micromolar/kg/day [6]
  Vd: The volume of distribution (Vd) of drug is 63.8 +/- 23.8 L [5]
  Water Solubility: The ability of drug to dissolve in water is measured as 50 mg/mL [4]
• Chemical Identifiers:
  Formula: C18H34N2O6S
  IUPAC Name: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
  Canonical SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@@H](C)O
  InChI: InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
  InChIKey: OJMMVQQUTAEWLP-KIDUDLJLSA-N
• Cross-matching ID:
  PubChem CID: 3000540
  ChEBI ID: CHEBI:6472
  CAS Number: 154-21-2
  DrugBank ID: DB01627
  TTD ID: D0Q0EX
  ACDINA ID: D01210

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial 50S ribosomal RNA (Bact 50S rRNA)	TTUWYEA	NOUNIPROTAC	Inhibitor	[7]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Lincomycin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Lincomycin and Atracurium.	Corneal disease [9A76-9A78]	[17]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Lincomycin 3g/10ml solution	3g/10ml	Solution	Intravenous; Intramuscular; Subconjunctival

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 050317.
• [2] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
• [3] FDA Approved Drug Products: Lincocin (lincomycin) injection
• [4] BDDCS applied to over 900 drugs
• [5] Gwilt PR, Smith RB: Protein binding and pharmacokinetics of lincomycin following intravenous administration of high doses. J Clin Pharmacol. 1986 Feb;26(2):87-90. doi: 10.1002/j.1552-4604.1986.tb02911.x.
• [6] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
• [7] Specific inhibition of 50S ribosomal subunit formation in Staphylococcus aureus cells by 16-membered macrolide, lincosamide, and streptogramin B antibiotics. Curr Microbiol. 2000 Aug;41(2):126-35.
• [8] A synthetic alanyl-initiator tRNA with initiator tRNA properties as determined by fluorescence measurements: comparison to a synthetic alanyl-elongator tRNA. Nucleic Acids Res. 1991 Oct 25;19(20):5749-54.
• [9] An examination of the differential sensitivity to ketolide antibiotics in ermB strains of Streptococcus pyogenes and Streptococcus pneumoniae. Curr Microbiol. 2004 Oct;49(4):239-47.
• [10] Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21.
• [11] Review of macrolides and ketolides: focus on respiratory tract infections. Drugs. 2001;61(4):443-98.
• [12] The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
• [13] Depression of colony formation by human thymus-derived lymphocytes with rifampin and other antimicrobial agents. J Infect Dis. 1981 Jun;143(6):832-5.
• [14] Retapamulin inhibition of translation and 50S ribosomal subunit formation in Staphylococcus aureus cells. Antimicrob Agents Chemother. 2007 Sep;51(9):3385-7.
• [15] The streptogramin antibiotics: update on their mechanism of action. Expert Opin Investig Drugs. 1998 Apr;7(4):591-9.
• [16] 2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
• [17] Alahdal O, Bevan DR "Clindamycin-induced neuromuscular blockade." Can J Anaesth 42 (1995): 614-7. [PMID: 7553999]