Details of the Drug

General Information of Drug (ID: DMSFQ8I)

Drug Name

Meclocycline

Synonyms

Meclociclina; Meclocyclinum; Meclosorb; Samil; Meclociclina [Italian]; GS 2989; GS-2989; Meclociclina [INN-Spanish]; Meclocycline(USAN); Meclocyclinum [INN-Latin]; Meclocycline (USAN/INN); Meclocycline [USAN:INN:BAN]; (2E,4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (2E,4aR,5S,5aS,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (2Z)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (2Z,4S,4aR,5S,5aR,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, [4S-(4.alpha.,4a.alpha.,5.alpha.,5a.alpha.,12a.alpha.)]-(9CI); 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, [4S-(4.alpha.,4aal; 2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methylidene-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; 7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide; 7-Chloro-6-methylene-5-oxytetracycline; 7-Cloro-6-metilene-5-ossitetraciclina; 7-Cloro-6-metilene-5-ossitetraciclina [Italian]; 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacene carboxamide

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

476.9

Logarithm of the Partition Coefficient (xlogp)

0.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Bioavailability: The bioavailability of drug is 66% [2]
Elimination: 40% of drug is excreted in urine and 43% of drug is excreted in fecal [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 5.6 hours [2]
Metabolism: The drug is not metabolised [2]
Vd: The volume of distribution (Vd) of drug is 121 L [2]

Chemical Identifiers

Formula: C22H21ClN2O8
IUPAC Name: (4S,4aR,5S,5aR,12aR)-7-chloro-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
Canonical SMILES: CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)C4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O
InChI: InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26-28,31,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1
InChIKey: RNIADBXQDMCFEN-IWVLMIASSA-N

Cross-matching ID

PubChem CID: 54676539
ChEBI ID: CHEBI:135772
CAS Number: 2013-58-3
DrugBank ID: DB13092
TTD ID: D07JHH

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Staphylococcus 30S ribosomal subunit (Stap-coc pbp2)	TTQ8KVI	F4NA87_STAAU	Binder	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
C-C motif chemokine 2 (CCL2)	OTAD2HEL	CCL2_HUMAN	Gene/Protein Processing	[4]
C-C motif chemokine 3 (CCL3)	OTW2H3ND	CCL3_HUMAN	Gene/Protein Processing	[4]
C-C motif chemokine 4 (CCL4)	OT6B8P25	CCL4_HUMAN	Gene/Protein Processing	[4]
C-C motif chemokine 5 (CCL5)	OTSCA5CK	CCL5_HUMAN	Gene/Protein Processing	[4]
Interleukin-6 receptor subunit alpha (IL6R)	OTCQL07Z	IL6RA_HUMAN	Gene/Protein Processing	[4]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[4]
Vascular endothelial growth factor A, long form	OTIM9MZ3	VEGFA_HUMAN	Gene/Protein Processing	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 065094.
2	Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1.
3	Detection of tetracycline resistance genes by PCR methods. Methods Mol Biol. 2004;268:3-13.
4	Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. Leuk Res. 2010 Jul;34(7):917-24. doi: 10.1016/j.leukres.2009.12.002. Epub 2010 Feb 8.