Details of the Drug

General Information of Drug (ID: DMVN5OH)

Drug Name

Minocycline

Synonyms

Borymycin; MINO; MIY; Minociclina; Minociclinum; Minocin; Minocline; Minocyclin; Minocyclinum; Minocycline Monohydrochloride; CL 59806; Lactoferrin B & Minocycline; Lactoferrin H & Minocycline; Minociclina [INN-Spanish]; Minocin (Hydrochloride); Minocin (TN); Minocyclinum [INN-Latin]; Vectrin (Hydrochloride); CRL-1605 & Minocycline; Minocycline (USAN/INN); Minocycline [USAN:BAN:INN]; (2Z,4S,4aS,5aR,12aS)-2-[amino(hydroxy)methylidene]-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; (4S,4AS,5AR,12AS)-4,7-BIS(DIMETHYLAMINO)-3,10,12,12A-TETRAHYDROXY-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE; 4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide; 7-Dimethylamino-6-demethyl-6-deoxytetracycline

Indication

Disease Entry	ICD 11	Status	REF
Acne vulgaris	ED80	Approved	[1]
Actinomycosis	N.A.	Approved	[1]
Acute gonococcal cervicitis	N.A.	Approved	[1]
Bacterial infection	1A00-1C4Z	Approved	[2]
Bartonellosis	N.A.	Approved	[1]
Bronchitis	CA20	Approved	[1]
Brucellosis	N.A.	Approved	[1]
Chancroid	N.A.	Approved	[1]
Listeriosis	N.A.	Approved	[1]
Lymphogranuloma venereum	N.A.	Approved	[1]
Ornithosis	N.A.	Approved	[1]
Periodontitis	DA0C	Approved	[1]
Pneumonia	CA40	Approved	[1]
Q fever	N.A.	Approved	[1]
Relapsing fever	N.A.	Approved	[1]
Rickettsialpox	N.A.	Approved	[1]
Rocky mountain spotted fever	N.A.	Approved	[1]
Syphilis	N.A.	Approved	[1]
Trachoma	N.A.	Approved	[1]
Tularemia	1B94	Approved	[1]
Typhus	N.A.	Approved	[1]
Urinary tract infection	GC08	Approved	[1]
Yaws	N.A.	Approved	[1]
Rosacea	ED90.0	Phase 2	[3]
Plague	N.A.	Investigative	[1]
Sinusitis	CA0A.Z	Investigative	[1]
Vibrio cholerae infection	1A00	Investigative	[1]


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Therapeutic Class

Antibiotics

Affected Organisms

Enteric bacteria and other eubacteriaBacillus anthracisListeria monocytogenesStaphylococcus aureusStreptococcus pneumoniaeFrancisella tularensisVibrio choleraeYersinia pestisAcinetobacterEnterobacter aerogenesEscherichia coliHaemophilus influenzaeKlebsiellaNeisseria gonorrhoeaeNeisseria meningitidisShigellaChlamydophila psittaciChlamydia trachomatisClostridiumFusobacterium nucleatumMycoplasma pneumoniaePropionibacterium acnesTreponema pallidum

ATC Code

A01AB23: Minocycline

A01AB: Antiinfectives and antiseptics for local oral treatment

A01A: STOMATOLOGICAL PREPARATIONS

A01: STOMATOLOGICAL PREPARATIONS

A: ALIMENTARY TRACT AND METABOLISM

D10AF07: Minocycline

D10AF: Antiinfectives for treatment of acne

D10A: ANTI-ACNE PREPARATIONS FOR TOPICAL USE

D10: ANTI-ACNE PREPARATIONS

D: DERMATOLOGICALS

J01AA08: Minocycline

J01AA: Tetracyclines

J01A: TETRACYCLINES

J01: ANTIBACTERIALS FOR SYSTEMIC USE

J: ANTIINFECTIVES FOR SYSTEMIC USE

J01AA08: Minocycline

J01AA: Tetracyclines

J01A: TETRACYCLINES

J01: ANTIBACTERIALS FOR SYSTEMIC USE

J: ANTIINFECTIVES FOR SYSTEMIC USE

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

457.5

Logarithm of the Partition Coefficient (xlogp)

-0.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 31.6 mgh/L [4]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 1.6 mg/L [4]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1.9 h [4]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [5]
Bioavailability: 97% of drug becomes completely available to its intended biological destination(s) [6]
Clearance: The clearance of drug is 3.36-5.7 L/h [4]
Elimination: 4.5-9% of an intravenous minocycline dose is recovered in the urine [7]
Half-life: The concentration or amount of drug in body reduced by one-half in 11.1 - 22.1 hours [8]
Metabolism: The drug is metabolized to 9-hydroxyminocycline [9]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 6.87 micromolar/kg/day [10]
Unbound Fraction: The unbound fraction of drug in plasma is 0.005% [11]
Vd: The volume of distribution (Vd) of drug is 67.5-115 L [4]
Water Solubility: The ability of drug to dissolve in water is measured as 50 mg/mL [5]

Chemical Identifiers

Formula: C23H27N3O7
IUPAC Name: (4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
Canonical SMILES: CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)N(C)C
InChI: InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27-28,31,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1
InChIKey: FFTVPQUHLQBXQZ-KVUCHLLUSA-N

Cross-matching ID

PubChem CID: 54675783
ChEBI ID: CHEMBL50694
CAS Number: 10118-90-8
UNII: FYY3R43WGO
DrugBank ID: DB01017
TTD ID: D08LTU
VARIDT ID: DR00568
ACDINA ID: D00437

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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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
Staphylococcus 30S ribosomal subunit (Stap-coc pbp2)	TTQ8KVI	F4NA87_STAAU	Binder	[12]

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 Minocycline (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Minocycline and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[13]
Sodium bicarbonate	DMMU6BJ	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Minocycline caused by Sodium bicarbonate mediated altered urine pH.	Acidosis [5C73]	[14]
Tromethamine	DMOBLGK	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Minocycline caused by Tromethamine mediated altered urine pH.	Acidosis [5C73]	[14]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Minocycline and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[15]
Aminophylline	DML2NIB	Moderate	Decreased metabolism of Minocycline caused by Aminophylline mediated inhibition of CYP450 enzyme.	Asthma [CA23]	[16]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Minocycline and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[17]
Mestranol	DMG3F94	Moderate	Decreased absorption of Minocycline due to formation of complexes caused by Mestranol.	Contraceptive management [QA21]	[18]
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Minocycline and Atracurium.	Corneal disease [9A76-9A78]	[19]
Mivacurium	DM473VD	Moderate	Additive neuromuscular blocking effects by the combination of Minocycline and Mivacurium.	Corneal disease [9A76-9A78]	[19]
Oxtriphylline	DMLHSE3	Moderate	Decreased metabolism of Minocycline caused by Oxtriphylline mediated inhibition of CYP450 enzyme.	Cough [MD12]	[16]
Mycophenolic acid	DMRBMAU	Moderate	Altered absorption of Minocycline due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[20]
SODIUM CITRATE	DMHPD2Y	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Minocycline caused by SODIUM CITRATE mediated altered urine pH.	Discovery agent [N.A.]	[14]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Minocycline and Cannabidiol.	Epileptic encephalopathy [8A62]	[21]
Digitoxin	DMWVIGP	Moderate	Altered absorption of Minocycline due to GI flora changes caused by Digitoxin.	Heart failure [BD10-BD1Z]	[22]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Minocycline and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[23]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Minocycline and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[24]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Minocycline and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[25]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Minocycline and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[26]
Sodium acetate anhydrous	DMH21E0	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Minocycline caused by Sodium acetate anhydrous mediated altered urine pH.	Hypo-osmolality/hyponatraemia [5C72]	[14]
Iron	DMAP8MV	Moderate	Decreased absorption of Minocycline due to formation of complexes caused by Iron.	Iron deficiency anaemia [3A00]	[27]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Minocycline and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[28]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Minocycline and Idelalisib.	Mature B-cell leukaemia [2A82]	[29]
Lanthanum carbonate	DMMJQSH	Moderate	Decreased absorption of Minocycline due to formation of complexes caused by Lanthanum carbonate.	Mineral absorption/transport disorder [5C64]	[25]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Minocycline and Leflunomide.	Rheumatoid arthritis [FA20]	[25]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Minocycline and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[21]
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Minocycline and Vecuronium.	Tonus and reflex abnormality [MB47]	[19]


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

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 27	E00381	83511	Colorant
D&C red no. 28	E00491	6097185	Colorant
D&C red no. 33	E00261	19116	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Hydrazine yellow	E00409	164825	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sodium stearyl fumarate	E00545	23665634	lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Ammonia	E00007	222	Alkalizing agent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
FD&C red no. 3	E00629	Not Available	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 6000	E00655	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Potassium hydroxide	E00233	14797	Alkalizing agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
Triethyl citrate	E00128	6506	Plasticizing agent; Solvent
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Water	E00035	962	Solvent


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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Minocycline 50 mg capsule	50 mg	Oral Capsule	Oral
Minocycline 45 mg capsule	45 mg	24 HR Extended Release Oral Capsule	Oral
Minocycline 135 mg capsule	135 mg	24 HR Extended Release Oral Capsule	Oral
Minocycline 100 mg capsule	100 mg	Oral Capsule	Oral
Minocycline 90 mg capsule	90 mg	24 HR Extended Release Oral Capsule	Oral
Minocycline 100 mg tablet	100 mg	Oral Tablet	Oral
Minocycline 50 mg tablet	50 mg	Oral Tablet	Oral
Minocycline 75 mg tablet	75 mg	Oral Tablet	Oral
Minocycline 75 mg capsule	75 mg	Oral Capsule	Oral
Minocycline 80 mg tablet	80 mg	24 HR Extended Release Oral Tablet	Oral
Minocycline 65 mg tablet	65 mg	24 HR Extended Release Oral Tablet	Oral
Minocycline 105 mg tablet	105 mg	24 HR Extended Release Oral Tablet	Oral
Minocycline 115 mg tablet	115 mg	24 HR Extended Release Oral Tablet	Oral
Minocycline 55 mg tablet	55 mg	24 HR Extended Release Oral Tablet	Oral
Minocycline 135 mg tablet	135 mg	24 HR Extended Release Oral Tablet	Oral
Minocycline 45 mg tablet	45 mg	24 HR Extended Release Oral Tablet	Oral
Minocycline 90 mg tablet	90 mg	24 HR Extended Release Oral Tablet	Oral

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References

1	Minocycline FDA Label
2	Emerging disease-modifying therapies for the treatment of motor neuron disease/amyotropic lateral sclerosis. Expert Opin Emerg Drugs. 2007 May;12(2):229-52.
3	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4	Saivin S, Houin G: Clinical pharmacokinetics of doxycycline and minocycline. Clin Pharmacokinet. 1988 Dec;15(6):355-66. doi: 10.2165/00003088-198815060-00001.
5	BDDCS applied to over 900 drugs
6	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
7	Welling PG, Shaw WR, Uman SJ, Tse FL, Craig WA: Pharmacokinetics of minocycline in renal failure. Antimicrob Agents Chemother. 1975 Nov;8(5):532-7. doi: 10.1128/aac.8.5.532.
8	FDA Approved Drug Products: Minocin Minocycline Oral Pellet-Filled Capsules
9	Simopoulos AP: The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases. Exp Biol Med (Maywood). 2008 Jun;233(6):674-88. doi: 10.3181/0711-MR-311. Epub 2008 Apr 11.
10	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
11	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
12	Functional, biophysical, and structural bases for antibacterial activity of tigecycline. Antimicrob Agents Chemother. 2006 Jun;50(6):2156-66.
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20	Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
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23	Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
24	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
25	Canadian Pharmacists Association.
26	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
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28	Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
29	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.