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]
Therapeutic Class
Antibiotics
Affected Organisms
Gram negative and gram positive bacteria
ATC Code
D10AF04: Meclocycline
D10AF: Antiinfectives for treatment of acne
D10A: ANTI-ACNE PREPARATIONS FOR TOPICAL USE
D10: ANTI-ACNE PREPARATIONS
D: DERMATOLOGICALS
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) 2
Hydrogen Bond Donor Count (hbonddonor) 6
Hydrogen Bond Acceptor Count (hbondacc) 9
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
CHEMBL135772
CAS Number
2013-58-3
UNII
23Q8M2HE6S
DrugBank ID
DB13092
TTD ID
D07JHH
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]

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]
Molecular Interaction Atlas (MIA) 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.