Details of the Drug

General Information of Drug (ID: DMBR5Q7)

Drug Name

Rolitetracycline

Synonyms

Bristacin; Kinteto; Pyrrolidinomethyltetracycline; Reverin; Revrin; Rolitetraciclina; Rolitetracyclinum; Solvocillin; Superciclin; Synotodecin; Synterin; Syntetrex; Syntetrin; Tetraverin; Transcycline; Velacicline; Velacycline; AAT 4; SQ 15659; Pirrolidinometil-tetraciclina; Pirrolidinometil-tetraciclina [Italian]; Prm-TC; Rolitetraciclina [INN-Spanish]; Rolitetracyclinum [INN-Latin]; SQ 15,659; Synterin (TN); N-(Pyrrolidinomethyl)tetracycline; Pyrrolidino-methyl-tetracycline; N-Pyrrolidino-methyl-tetracycline; Rolitetracycline (JAN/USAN/INN); Rolitetracycline [USAN:INN:BAN:JAN]; N-(1-Pyrrolidinylmethyl)-tetracycline; (2Z,4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-2-[hydroxy-(pyrrolidin-1-ylmethylamino)methylidene]-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (2Z,4S,4aS,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-2-[hydroxy-(pyrrolidin-1-ylmethylamino)methylidene]-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (2Z,4S,6S,12aS)-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-2-[hydroxy-(pyrrolidin-1-ylmethylamino)methylidene]-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione; (4S,4aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(pyrrolidin-1-ylmethyl)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-2-naphthacenecarboxamide

Indication

Disease Entry	ICD 11	Status	REF
Acne vulgaris	ED80	Approved	[1]
------------------------------------------------------------------------------------

Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

527.6

Logarithm of the Partition Coefficient (xlogp)

-0.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 0.97 mL/min/kg [3]
Elimination: 55% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 8.8 hours [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 11.05047 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.5% [3]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.54 L/kg [3]
Water Solubility: The ability of drug to dissolve in water is measured as 1250 mg/mL [2]

Chemical Identifiers

Formula: C27H33N3O8
IUPAC Name: (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-N-(pyrrolidin-1-ylmethyl)-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
Canonical SMILES: C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)NCN5CCCC5)N(C)C)O
InChI: InChI=1S/C27H33N3O8/c1-26(37)13-7-6-8-16(31)17(13)21(32)18-14(26)11-15-20(29(2)3)22(33)19(24(35)27(15,38)23(18)34)25(36)28-12-30-9-4-5-10-30/h6-8,14-15,20,31-32,35,37-38H,4-5,9-12H2,1-3H3,(H,28,36)/t14-,15-,20-,26+,27-/m0/s1
InChIKey: IKQRPFTXKQQLJF-IAHYZSEUSA-N

Cross-matching ID

PubChem CID: 54682938
ChEBI ID: CHEBI:63334
CAS Number: 751-97-3
DrugBank ID: DB01301
TTD ID: D05AFR

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	[1]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Reversed-phase high-performance liquid chromatography coupled to ultraviolet and electrospray time-of-flight mass spectrometry on-line detection fo... J Chromatogr A. 2008 Jun 27;1195(1-2):107-16.
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	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