Details of the Drug

General Information of Drug (ID: DMKECZD)

Drug Name

Temozolomide

Synonyms

Methazolastone; Temodal; Temodar; Temozolamide; Temozolodida; Temozolomidum; Essex brand of temozolomide; Scheringbrand of temozolomide; Temozolodida [Spanish]; Temozolomidum [Latin]; M B 39831; MB 39831; Sch 52365; M & B 39831; M&B 39831; M-39831; Sch-52365; Schering-Plough brand of temozolomide; TMZ-Bioshuttle; Temodal (TN); Temodar (TN); Temozolomide [INN:BAN]; M&B-39831; Temozolomide (JAN/USAN/INN); 3,4-Dihydro-3-methyl-4-oxoimidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxamide; 3,4-Dihydro-3-methyl-4-oxoimidazo(5,1-d)-as-tetrazine-8-carboxamide; 3-Methyl-4-oxo-3,4-dihydroimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamide; 3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetraazine-8-carboxamide; 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide; 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide; 8-Carbamoyl-3-methylimidazo(5,1-d)-1,2,3,5-tetrazin-4(3H)-one; TMZ

Indication

Disease Entry	ICD 11	Status	REF
Adenocarcinoma	2D40	Approved	[1]
Astrocytoma	2A00.0Y	Approved	[1]
Brain disease	8C70-8E61	Approved	[1]
Central nervous system disease	8A04-8D87	Approved	[1]
Cutaneous melanoma	2C30	Approved	[1]
Glioblastoma	2A00	Approved	[1]
Glioblastoma of brain	2A00.00	Approved	[1]
Gliosarcoma	N.A.	Approved	[1]
Grade IV astrocytoma	2A00.0	Approved	[2]
Kidney neoplasm	N.A.	Approved	[1]
Lung cancer	2C25.0	Approved	[1]
Malignant glioma	2A00.0	Approved	[1]
Melanoma	2C30	Approved	[1]
Neuroblastoma	2D11.2	Investigative	[1]
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Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

194.15

Logarithm of the Partition Coefficient (xlogp)

-1.1

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 23.4 mgh/L [3]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 7.5 mg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1 h [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Bioavailability: 96% of drug becomes completely available to its intended biological destination(s) [5]
Clearance: The drug present in the plasma can be removed from the body at the rate of 3.6 mL/min/kg [6]
Elimination: Roughly 38% of administered temozolomide can be recovered over seven days, with 38% in the urine and only 0.8% in the feces [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 1.8 hours [3]
Metabolism: The drug is metabolized via the nonenzymatic chemical conversion to the active metabolite [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 25.4585 micromolar/kg/day [7]
Vd: The volume of distribution (Vd) of drug is 0.4 L/kg [3]

Chemical Identifiers

Formula: C6H6N6O2
IUPAC Name: 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
Canonical SMILES: CN1C(=O)N2C=NC(=C2N=N1)C(=O)N
InChI: InChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13)
InChIKey: BPEGJWRSRHCHSN-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5394
ChEBI ID: CHEBI:72564
CAS Number: 85622-93-1
DrugBank ID: DB00853
TTD ID: D0C8EU
ACDINA ID: D00660

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
Human Deoxyribonucleic acid (hDNA)	TTUTN1I	NOUNIPROTAC	Modulator	[8]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
(E2-independent) E3 ubiquitin-conjugating enzyme FATS (C10ORF90)	OT6DNZC4	CJ090_HUMAN	Gene/Protein Processing	[9]
(E3-independent) E2 ubiquitin-conjugating enzyme	OTHGS2VA	UBE2O_HUMAN	Gene/Protein Processing	[9]
1-acyl-sn-glycerol-3-phosphate acyltransferase beta (AGPAT2)	OT5I4Y9K	PLCB_HUMAN	Gene/Protein Processing	[9]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1 (PLCB1)	OT9HYT7A	PLCB1_HUMAN	Gene/Protein Processing	[9]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase eta-1 (PLCH1)	OT6Z1L2E	PLCH1_HUMAN	Gene/Protein Processing	[9]
14-3-3 protein beta/alpha	OTGBS3RF	1433B_HUMAN	Gene/Protein Processing	[9]
17-beta-hydroxysteroid dehydrogenase 14 (HSD17B14)	OT0ETO72	DHB14_HUMAN	Gene/Protein Processing	[9]
182 kDa tankyrase-1-binding protein (TNKS1BP1)	OTBIZECQ	TB182_HUMAN	Gene/Protein Processing	[9]
2'-5'-oligoadenylate synthase 1 (OAS1)	OT8ZLOCY	OAS1_HUMAN	Gene/Protein Processing	[9]
2'-5'-oligoadenylate synthase 2 (OAS2)	OT64CCTM	OAS2_HUMAN	Gene/Protein Processing	[9]

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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 Temozolomide (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Temozolomide and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[10]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Temozolomide and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[11]
Roflumilast	DMPGHY8	Moderate	Additive immunosuppressive effects by the combination of Temozolomide and Roflumilast.	Asthma [CA23]	[12]
Ofloxacin	DM0VQN3	Minor	Decreased absorption of Temozolomide due to intestinal mucosa variation caused by Ofloxacin.	Bacterial infection [1A00-1C4Z]	[13]
Sparfloxacin	DMB4HCT	Minor	Decreased absorption of Temozolomide due to intestinal mucosa variation caused by Sparfloxacin.	Bacterial infection [1A00-1C4Z]	[13]
Gemifloxacin	DMHT34O	Minor	Decreased absorption of Temozolomide due to intestinal mucosa variation caused by Gemifloxacin.	Bacterial infection [1A00-1C4Z]	[13]
Norfloxacin	DMIZ6W2	Minor	Decreased absorption of Temozolomide due to intestinal mucosa variation caused by Norfloxacin.	Bacterial infection [1A00-1C4Z]	[13]
ABT-492	DMJFD2I	Minor	Decreased absorption of Temozolomide due to intestinal mucosa variation caused by ABT-492.	Bacterial infection [1A00-1C4Z]	[13]
Levofloxacin	DMS60RB	Minor	Decreased absorption of Temozolomide due to intestinal mucosa variation caused by Levofloxacin.	Bacterial infection [1A00-1C4Z]	[13]
Lomefloxacin	DMVRH9C	Minor	Decreased absorption of Temozolomide due to intestinal mucosa variation caused by Lomefloxacin.	Bacterial infection [1A00-1C4Z]	[13]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Temozolomide and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[14]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Temozolomide and Cannabidiol.	Epileptic encephalopathy [8A62]	[12]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Temozolomide and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[15]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Temozolomide and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[16]
Teriflunomide	DMQ2FKJ	Major	Additive immunosuppressive effects by the combination of Temozolomide and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[17]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Temozolomide and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[18]
Denosumab	DMNI0KO	Moderate	Additive immunosuppressive effects by the combination of Temozolomide and Denosumab.	Low bone mass disorder [FB83]	[19]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Temozolomide and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[20]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Temozolomide and Idelalisib.	Mature B-cell leukaemia [2A82]	[21]
Thalidomide	DM70BU5	Major	Additive thrombogenic effects by the combination of Temozolomide and Thalidomide.	Multiple myeloma [2A83]	[22]
Tecfidera	DM2OVDT	Moderate	Additive immunosuppressive effects by the combination of Temozolomide and Tecfidera.	Multiple sclerosis [8A40]	[23]
Siponimod	DM2R86O	Major	Additive immunosuppressive effects by the combination of Temozolomide and Siponimod.	Multiple sclerosis [8A40]	[10]
Fingolimod	DM5JVAN	Major	Additive immunosuppressive effects by the combination of Temozolomide and Fingolimod.	Multiple sclerosis [8A40]	[24]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Temozolomide and Ocrelizumab.	Multiple sclerosis [8A40]	[25]
Ozanimod	DMT6AM2	Major	Additive immunosuppressive effects by the combination of Temozolomide and Ozanimod.	Multiple sclerosis [8A40]	[12]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive myelosuppressive effects by the combination of Temozolomide and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[26]
Gatifloxacin	DMSL679	Minor	Decreased absorption of Temozolomide due to intestinal mucosa variation caused by Gatifloxacin.	Respiratory infection [CA07-CA4Z]	[13]
Canakinumab	DM8HLO5	Moderate	Additive immunosuppressive effects by the combination of Temozolomide and Canakinumab.	Rheumatoid arthritis [FA20]	[27]
Golimumab	DMHZV7X	Major	Additive immunosuppressive effects by the combination of Temozolomide and Golimumab.	Rheumatoid arthritis [FA20]	[28]
Anthrax vaccine	DM9GSWY	Moderate	Antagonize the effect of Temozolomide when combined with Anthrax vaccine.	Sepsis [1G40-1G41]	[29]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Temozolomide and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[12]
Azathioprine	DMMZSXQ	Moderate	Additive myelosuppressive effects by the combination of Temozolomide and Azathioprine.	Transplant rejection [NE84]	[10]
Ganciclovir	DM1MBYQ	Moderate	Additive myelosuppressive effects by the combination of Temozolomide and Ganciclovir.	Virus infection [1A24-1D9Z]	[10]
Valganciclovir	DMS2IUH	Moderate	Additive myelosuppressive effects by the combination of Temozolomide and Valganciclovir.	Virus infection [1A24-1D9Z]	[10]
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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. 28	E00491	6097185	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
Kyselina citronova	E00014	311	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
methylparaben	E00149	7456	Antimicrobial preservative
Propyl 4-hydroxybenzoate	E00141	7175	Antimicrobial preservative
Propylparaben sodium	E00567	23679044	Antimicrobial preservative
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sodium methylparaben	E00543	23663626	Antimicrobial preservative
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
Carmellose sodium	E00625	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
Isobutyl alcohol	E00130	6560	Flavoring agent; Solvent
Lithol rubin BCA	E00607	135423095	Colorant
Magnesium stearate	E00208	11177	lubricant
Potassium hydroxide	E00233	14797	Alkalizing agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium hydroxide	E00234	14798	Alkalizing agent
Tartaric acid	E00029	875	Acidulant; Complexing agent; Flavoring agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Temozolomide 5 mg capsule	5 mg	Oral Capsule	Oral
Temozolomide 140 mg capsule	140 mg	Oral Capsule	Oral
Temozolomide 180 mg capsule	180 mg	Oral Capsule	Oral
Temozolomide 20 mg capsule	20 mg	Oral Capsule	Oral
Temozolomide 100 mg capsule	100 mg	Oral Capsule	Oral
Temozolomide 250 mg capsule	250 mg	Oral Capsule	Oral

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References

1	Temozolomide FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7301).
3	FDA Approved Drug Products: TEMODAR (temozolomide) capsules and injection
4	BDDCS applied to over 900 drugs
5	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
6	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7	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
8	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
9	Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
10	Cerner Multum, Inc. "Australian Product Information.".
11	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
12	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
13	Johnson EJ, MacGowan AP, Potter MN, et al "Reduced absorption of oral ciprofloxacin after chemotherapy for haematological malignancy." J Antimicrob Chemother 25 (1990): 837-42. [PMID: 2373666]
14	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
15	Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
16	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
17	Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
18	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
19	Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA.
20	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]
21	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
22	Bennett CL, Nebeker JR, Samore MH, et al "The Research on Adverse Drug Events and Reports (RADAR) project." JAMA 293 (2005): 2131-40. [PMID: 15870417]
23	Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
24	Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
25	Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
26	Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
27	Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY.
28	Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA.
29	CDC. Centers for Disease Control and Prevention/ "Recommendations of the advisory committtee on immunization practices (ACIP): use of vaccines and immune globulins in persons with altered immunocompetence." MMWR Morb Mortal Wkly Rep 42(RR-04) (1993): 1-18. [PMID: 20300058]