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]
Pneumococcal infection	CA00-CA40	Approved	[2]
Streptococcus infection	1B53	Approved	[2]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

406.5

Logarithm of the Partition Coefficient (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

Repurposed Drugs (RPD)

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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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
HLA class I histocompatibility antigen, alpha chain E (HLA-E)	OTX1CTFB	HLAE_HUMAN	Gene/Protein Processing	[8]
Major histocompatibility complex class I-related gene protein (MR1)	OTZU3XX7	HMR1_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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]	[9]
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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
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Pharmaceutical Formulation

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

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References

1	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 050317.
2	Lincomycin FDA Label
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	Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. Chem Res Toxicol. 2015 May 18;28(5):927-34. doi: 10.1021/tx5005248. Epub 2015 Apr 3.
9	Alahdal O, Bevan DR "Clindamycin-induced neuromuscular blockade." Can J Anaesth 42 (1995): 614-7. [PMID: 7553999]