Details of Drug

Drug General Information (ID: D0425)
Drug Name	Darolutamide
Drug Type	Small molecule
Drug Synonymous	1297538-32-9; BAY-1841788; N-((S)-1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide; Darolutamide [USAN]; Darolutamide (JAN/USAN/INN); SCHEMBL1814935; SCHEMBL13733117; KS-00000TSX; EX-A759; BLIJXOOIHRSQRB-PXYINDEMSA-N; MolPort-046-033-692; MolPort-044-560-277; AKOS030526387; CS-5174; BAY1841788; DB12941; BAY 1841788; HY-16985; S7559; FT-0700158; J3.501.129C; D11045; J-690121; 1H-Pyrazole-3-carboxamide, N-((1S)-2-(3-(3-chloro-4-cyanophen Click to Show/Hide
Disease Class	2C82: Prostate cancer
Therapeutic Class	Antiandrogens
Structure
Structure	3D Structure		2D Structure
Formula	C19H19ClN6O2
InChI	1S/C19H19ClN6O2/c1-11(22-19(28)18-8-17(12(2)27)23-24-18)10-26-6-5-16(25-26)13-3-4-14(9-21)15(20)7-13/h3-8,11-12,27H,10H2,1-2H3,(H,22,28)(H,23,24)/t11-,12?/m0/s1
InChIKey	BLIJXOOIHRSQRB-PXYINDEMSA-N
Canonical SMILES	CC(CN1C=CC(=N1)C2=CC(=C(C=C2)C#N)Cl)NC(=O)C3=NNC(=C3)C(C)O
External Link
	Pubchem ID	67171867
	CAS Number	1297538-32-9
	TTD ID	D0DV6D
	INTEDE ID	DR0419

Drug-Drug Interaction Network
Sunburst Graph		Legend Information AM002 Affected cellular transport AM004 Affected intra/extra-hepatic metabolism BM010 Transporter inhibition BM011 Transporter induction BM017 CYP450 enzyme inhibition BM022 CYP450 enzyme induction
Relation Graph

Full list of drugs interacting with Darolutamide
Affected cellular transport
	Transporter inhibition					Drug Num: 61
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0171		Berotralstat	C30H26F4N6O	137528262	Major		Inter Info	[2]
D0562		Eluxadoline	C32H35N5O5	11250029	Major		Inter Info	[3], [4], [5]
D0739		Grazoprevir	C38H50N6O9S	44603531	Major		Inter Info	[3], [6], [7]
D1430		Rosuvastatin	C22H28FN3O6S	446157	Major		Inter Info	[3], [10], [1]
D0026		Afatinib	C24H25ClFN5O3	10184653	Moderate		Inter Info	[1]
D0053		Ambrisentan	C22H22N2O4	6918493	Moderate		Inter Info	[3], [1]
D0109		Artesunate	C19H28O8	6917864	Moderate		Inter Info	[1]
D0120		Atorvastatin	C33H35FN2O5	60823	Moderate		Inter Info	[1]
D0182		Binimetinib	C17H15BrF2N4O3	10288191	Moderate		Inter Info	[11], [3], [12]
D0303		Cerivastatin	C26H34FNO5	446156	Moderate		Inter Info	[3], [1]
D0348		Cladribine	C10H12ClN5O3	20279	Moderate		Inter Info	[1]
D0726		Glecaprevir	C38H46F4N6O9S	66828839	Moderate		Inter Info	[3], [14], [1]
D0963		Lusutrombopag	C29H32Cl2N2O5S	49843517	Moderate		Inter Info	[15]
D1663		Ubrogepant	C29H26F3N5O3	68748835	Moderate		Inter Info	[16]
D0429		Daunorubicin	C27H29NO10	30323	Moderate		Inter Info	[1]
D0430		Daunorubicin (liposomal)	C27H29NO10	30323	Moderate		Inter Info	[1], [17]
D0438		Delafloxacin	C18H12ClF3N4O4	487101	Moderate		Inter Info	[1]
D0528		Doxorubicin	C27H29NO11	31703	Moderate		Inter Info	[1]
D0529		Doxorubicin (liposomal)	C27H29NO11	31703	Moderate		Inter Info	[1], [17]
D0561		Eltrombopag	C25H22N4O4	135449332	Moderate		Inter Info	[1]
D0565		Empagliflozin	C23H27ClO7	11949646	Moderate		Inter Info	[1]
D0631		Ezetimibe	C24H21F2NO3	150311	Moderate		Inter Info	[3], [1]
D0656		Fexofenadine	C32H39NO4	3348	Moderate		Inter Info	[3], [1]
D0686		Fluvastatin	C24H26FNO4	446155	Moderate		Inter Info	[3], [1]
D0730		Glyburide	C23H28ClN3O5S	3488	Moderate		Inter Info	[3], [1]
D0789		Idelalisib	C22H18FN7O	11625818	Moderate		Inter Info	[1]
D0793		Imatinib	C29H31N7O	5291	Moderate		Inter Info	[1]
D0845		Irinotecan	C33H38N4O6	60838	Moderate		Inter Info	[1]
D0846		Irinotecan (liposomal)	C33H38N4O6	60838	Moderate		Inter Info	[1], [17]
D0894		Lapatinib	C29H26ClFN4O4S	208908	Moderate		Inter Info	[1]
D0956		Lovastatin	C24H36O5	53232	Moderate		Inter Info	[3], [1]
D0961		Lurasidone	C28H36N4O2S	213046	Moderate		Inter Info	[1]
D1025		Methotrexate	C20H22N8O5	126941	Moderate		Inter Info	[1]
D1079		Mitoxantrone	C22H28N4O6	4212	Moderate		Inter Info	[1]
D1140		Niraparib	C19H20N4O	24958200	Moderate		Inter Info	[1]
D1170		Olmesartan	C24H26N6O3	158781	Moderate		Inter Info	[3], [1]
D1190		Osimertinib	C28H33N7O2	71496458	Moderate		Inter Info	[1]
D1211		Ozanimod	C23H24N4O3	52938427	Moderate		Inter Info	[1]
D1232		Pazopanib	C21H23N7O2S	10113978	Moderate		Inter Info	[1]
D1301		Pitavastatin	C25H24FNO4	5282452	Moderate		Inter Info	[3], [1]
D1329		Pravastatin	C23H36O7	54687	Moderate		Inter Info	[3], [1]
D1392		Repaglinide	C27H36N2O4	65981	Moderate		Inter Info	[3], [1]
D1396		Revefenacin	C35H43N5O4	11753673	Moderate		Inter Info	[20], [6], [21]
D1402		Rifaximin	C43H51N3O11	6436173	Moderate		Inter Info	[3], [1]
D1407		Rimegepant	C28H28F2N6O3	51049968	Moderate		Inter Info	[22]
D1417		Rivaroxaban	C19H18ClN3O5S	9875401	Moderate		Inter Info	[1]
D1432		Rucaparib	C19H18FN3O	9931954	Moderate		Inter Info	[1]
D1457		Selexipag	C26H32N4O4S	9913767	Moderate		Inter Info	[1]
D1471		Simeprevir	C38H47N5O7S2	24873435	Moderate		Inter Info	[3], [1]
D1473		Simvastatin	C25H38O5	54454	Moderate		Inter Info	[3], [1]
D1517		Sulfasalazine	C18H14N4O5S	5339	Moderate		Inter Info	[1]
D1532		Talazoparib	C19H14F2N6O	135565082	Moderate		Inter Info	[23]
D1556		Teriflunomide	C12H9F3N2O2	54684141	Moderate		Inter Info	[1]
D1610		Topotecan	C23H23N3O5	60700	Moderate		Inter Info	[1]
D1687		Vemurafenib	C23H18ClF2N3O3S	42611257	Moderate		Inter Info	[1]
D1688		Venetoclax	C45H50ClN7O7S	49846579	Moderate		Inter Info	[1]
D0313		Chloramphenicol	C11H12Cl2N2O5	5959	Minor		Inter Info	[1]
D0720		Gilteritinib	C29H44N8O3	49803313	Minor		Inter Info	[1]
D0725		Glasdegib	C21H22N6O	25166913	Minor		Inter Info	[1]
D1134		Nifedipine	C17H18N2O6	4485	Minor		Inter Info	[1]
D1353		Propafenone	C21H27NO3	4932	Minor		Inter Info	[1]
Affected intra/extra-hepatic metabolism
	CYP450 enzyme inhibition					Drug Num: 58
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0116		Atazanavir	C38H52N6O7	148192	Moderate		Inter Info	[1]
D0192		Boceprevir	C27H45N5O5	10324367	Moderate		Inter Info	[1]
D0375		Cobicistat	C40H53N7O5S2	25151504	Moderate		Inter Info	[1]
D0386		Conivaptan	C32H26N4O2	151171	Moderate		Inter Info	[1]
D0799		Indinavir	C36H47N5O4	5362440	Moderate		Inter Info	[1]
D0867		Itraconazole	C35H38Cl2N8O4	55283	Moderate		Inter Info	[1]
D0880		Ketoconazole	C26H28Cl2N4O4	456201	Moderate		Inter Info	[1]
D0946		Lonafarnib	C27H31Br2ClN4O2	148195	Moderate		Inter Info	[1]
D1119		Nelfinavir	C32H45N3O4S	64143	Moderate		Inter Info	[1]
D1315		Posaconazole	C37H42F2N8O4	468595	Moderate		Inter Info	[1]
D1415		Ritonavir	C37H48N6O5S2	392622	Moderate		Inter Info	[1]
D1444		Saquinavir	C38H50N6O5	441243	Moderate		Inter Info	[1]
D1541		Telaprevir	C36H53N7O6	3010818	Moderate		Inter Info	[1]
D1544		Telithromycin	C43H65N5O10	3002190	Moderate		Inter Info	[1]
D1660		Tucatinib	C26H24N8O2	51039094	Moderate		Inter Info	[1]
D0007		Abiraterone	C24H31NO	132971	Minor		Inter Info	[1]
D0066		Amiodarone	C25H29I2NO3	2157	Minor		Inter Info	[1]
D0069		Amlodipine	C20H25ClN2O5	2162	Minor		Inter Info	[1]
D0080		Amprenavir	C25H35N3O6S	65016	Minor		Inter Info	[1]
D0100		Aprepitant	C23H21F7N4O3	135413536	Minor		Inter Info	[1]
D0302		Ceritinib	C28H36ClN5O3S	57379345	Minor		Inter Info	[1]
D0337		Cimetidine	C10H16N6S	2756	Minor		Inter Info	[1]
D0341		Ciprofloxacin	C17H18FN3O3	2764	Minor		Inter Info	[1]
D0393		Crizotinib	C21H22Cl2FN5O	11626560	Minor		Inter Info	[1]
D0413		Dalfopristin	C34H50N4O9S	6323289	Minor		Inter Info	[1]
D0696		Fosnetupitant	C31H35F6N4O5P	71544786	Minor		Inter Info	[1]
D0896		Larotrectinib	C21H22F2N6O2	46188928	Minor		Inter Info	[1]
D1459		Selpercatinib	C29H31N7O3	134436906	Minor		Inter Info	[1]
D1653		Troleandomycin	C41H67NO15	202225	Minor		Inter Info	[1]
D1709		Voxelotor	C19H19N3O3	71602803	Minor		Inter Info	[1]
D0426		Darunavir	C27H37N3O7S	213039	Minor		Inter Info	[1]
D0439		Delavirdine	C22H28N6O3S	5625	Minor		Inter Info	[1]
D0534		Dronedarone	C31H44N2O5S	208898	Minor		Inter Info	[1]
D0543		Duvelisib	C22H17ClN6O	50905713	Minor		Inter Info	[1]
D0577		Entrectinib	C31H34F2N6O2	25141092	Minor		Inter Info	[1]
D0597		Erythromycin	C37H67NO13	12560	Minor		Inter Info	[1]
D0638		Fedratinib	C27H36N6O3S	16722836	Minor		Inter Info	[1]
D0667		Fluconazole	C13H12F2N6O	3365	Minor		Inter Info	[1]
D0687		Fluvoxamine	C15H21F3N2O2	5324346	Minor		Inter Info	[1]
D0692		Fosamprenavir	C25H36N3O9PS	131536	Minor		Inter Info	[1]
D0693		Fosaprepitant	C23H22F7N4O6P	135413538	Minor		Inter Info	[1]
D0852		Isavuconazonium	C35H35F2N8O5S+	6918606	Minor		Inter Info	[1]
D0891		Lanreotide	C54H69N11O10S2	71349	Minor		Inter Info	[1]
D0906		Letermovir	C29H28F4N4O4	45138674	Minor		Inter Info	[1]
D0911		Levamlodipine	C20H25ClN2O5	9822750	Minor		Inter Info	[1]
D1057		Miconazole	C18H14Cl4N2O	4189	Minor		Inter Info	[1]
D1117		Nefazodone	C25H32ClN5O2	4449	Minor		Inter Info	[1]
D1127		Netupitant	C30H32F6N4O	6451149	Minor		Inter Info	[1]
D1136		Nilotinib	C28H22F3N7O	644241	Minor		Inter Info	[1]
D1163		Octreotide	C49H66N10O10S2	448601	Minor		Inter Info	[1]
D1189		Osilodrostat	C13H10FN3	44139752	Minor		Inter Info	[1]
D1230		Pasireotide	C58H66N10O9	9941444	Minor		Inter Info	[1]
D1383		Ranolazine	C24H33N3O4	56959	Minor		Inter Info	[1]
D1398		Ribociclib	C23H30N8O	44631912	Minor		Inter Info	[1]
D1505		Stiripentol	C14H18O3	5311454	Minor		Inter Info	[1]
D1608		Tolvaptan	C26H25ClN2O3	216237	Minor		Inter Info	[1]
D1690		Verapamil	C27H38N2O4	2520	Minor		Inter Info	[1]
D1706		Voriconazole	C16H14F3N5O	71616	Minor		Inter Info	[1]
	CYP450 enzyme induction					Drug Num: 51
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0095		Apalutamide	C21H15F4N5O2S	24872560	Major		Inter Info	[1]
D0255		Carbamazepine	C15H12N2O	2554	Major		Inter Info	[1]
D0453		Dexamethasone	C22H29FO5	5743	Major		Inter Info	[1]
D0578		Enzalutamide	C21H16F4N4O2S	15951529	Major		Inter Info	[1]
D0697		Fosphenytoin	C16H15N2O6P	56339	Major		Inter Info	[1]
D0953		Lorlatinib	C21H19FN6O2	71731823	Major		Inter Info	[1]
D0958		Lumacaftor	C24H18F2N2O5	16678941	Major		Inter Info	[8], [1], [9]
D1265		Phenobarbital	C12H12N2O3	4763	Major		Inter Info	[1]
D1283		Phenytoin	C15H12N2O2	1775	Major		Inter Info	[1]
D1340		Primidone	C12H14N2O2	4909	Major		Inter Info	[1]
D1400		Rifampicin	C43H58N4O12	135398735	Major		Inter Info	[8], [1], [9]
D1401		Rifapentine	C47H64N4O12	135403821	Major		Inter Info	[1]
D1502		St. John's Wort	NA	NA	Major		Inter Info	[1]
D0061		Aminoglutethimide	C13H16N2O2	2145	Moderate		Inter Info	[1]
D0071		Amobarbital	C11H18N2O3	2164	Moderate		Inter Info	[1]
D0106		Armodafinil	C15H15NO2S	9690109	Moderate		Inter Info	[1]
D0178		Bexarotene	C24H28O2	82146	Moderate		Inter Info	[1]
D0194		Bosentan	C27H29N5O6S	104865	Moderate		Inter Info	[1]
D0204		Brigatinib	C29H39ClN7O2P	68165256	Moderate		Inter Info	[1]
D0224		Butabarbital	C10H16N2O3	2479	Moderate		Inter Info	[1]
D0225		Butalbital	C11H16N2O3	2481	Moderate		Inter Info	[1]
D0300		Cenobamate	C10H10ClN5O2	11962412	Moderate		Inter Info	[1]
D0406		Dabrafenib	C23H20F3N5O2S2	44462760	Moderate		Inter Info	[3], [13]
D0601		Eslicarbazepine	C15H14N2O2	9881504	Moderate		Inter Info	[1]
D0872		Ivosidenib	C28H22ClF3N6O3	71657455	Moderate		Inter Info	[1]
D1258		Pexidartinib	C20H15ClF3N5	25151352	Moderate		Inter Info	[1]
D0432		Deferasirox	C21H15N3O4	214348	Moderate		Inter Info	[1]
D0554		Efavirenz	C14H9ClF3NO2	64139	Moderate		Inter Info	[1]
D0555		Elagolix	C32H30F5N3O5	11250647	Moderate		Inter Info	[1]
D0628		Etravirine	C20H15BrN6O	193962	Moderate		Inter Info	[1]
D0639		Felbamate	C11H14N2O4	3331	Moderate		Inter Info	[1]
D0732		Glycerol phenylbutyrate	C33H38O6	10482134	Moderate		Inter Info	[1]
D0741		Griseofulvin	C17H17ClO6	441140	Moderate		Inter Info	[1]
D0901		Lemborexant	C22H20F2N4O2	56944144	Moderate		Inter Info	[18], [1], [19]
D0905		Lesinurad	C17H14BrN3O2S	53465279	Moderate		Inter Info	[1]
D1040		Methylphenobarbital	C13H14N2O3	8271	Moderate		Inter Info	[18], [1], [19]
D1078		Mitotane	C14H10Cl4	4211	Moderate		Inter Info	[1]
D1081		Modafinil	C15H15NO2S	4236	Moderate		Inter Info	[1]
D1099		Nafcillin	C21H22N2O5S	8982	Moderate		Inter Info	[1]
D1128		Nevirapine	C15H14N4O	4463	Moderate		Inter Info	[1]
D1186		Oritavancin	C86H97Cl3N10O26	16136912	Moderate		Inter Info	[1]
D1198		Oxcarbazepine	C15H12N2O2	34312	Moderate		Inter Info	[1]
D1248		Pentobarbital	C11H18N2O3	4737	Moderate		Inter Info	[1]
D1274		Phenylbutazone	C19H20N2O2	4781	Moderate		Inter Info	[1]
D1399		Rifabutin	C46H62N4O11	135398743	Moderate		Inter Info	[1]
D1433		Rufinamide	C10H8F2N4O	129228	Moderate		Inter Info	[1]
D1453		Secobarbital	C12H18N2O3	5193	Moderate		Inter Info	[1]
D1518		Sulfinpyrazone	C23H20N2O3S	5342	Moderate		Inter Info	[1]
D1538		Tazemetostat	C34H44N4O4	66558664	Moderate		Inter Info	[1]
D1546		Telotristat ethyl	C27H26ClF3N6O3	25181577	Moderate		Inter Info	[18], [1], [19]
D1652		Troglitazone	C24H27NO5S	5591	Moderate		Inter Info	[1]

References
1	Product Information. Nubeqa (darolutamide). Bayer HealthCare Pharmaceuticals Inc., Whippany, NJ.
2	Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
3	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
4	Davenport JM, Covington P, Bonifacio L, McIntyre G, Venitz J "Effect of uptake transporters OAT3 and OATPIBI and efflux transporter MRP2 on the pharmacokinetics of eluxadoline." J Clin Pharmacol 55 (2015): 534-42. [PMID: 25491493]
5	Product Information. Viberzi (eluxadoline). Actavis Pharma, Inc., Parsippany, NJ.
6	Product Information. Nexlizet (bempedoic acid-ezetimibe). Esperion Therapeutics, Ann Arbor, MI.
7	Product Information. Zepatier (elbasvir-grazoprevir). Merck &amp Company Inc, Whitehouse Station, NJ.
8	Product Information. Kalydeco (ivacaftor). Vertex Pharmaceuticals, Cambridge, MA.
9	Product Information. Trikafta (elexacaftor/ivacaftor/tezacaftor). Vertex Pharmaceuticals, Cambridge, MA.
10	Product Information. Crestor (rosuvastatin). AstraZeneca Pharma Inc, Mississauga, ON.
11	Cerner Multum, Inc. "Australian Product Information.".
12	Product Information. Mektovi (binimetinib). Array BioPharma Inc., Boulder, CO.
13	Product Information. Tafinlar (dabrafenib). GlaxoSmithKline, Research Triangle Park, NC.
14	Product Information. Mavyret (glecaprevir-pibrentasvir). Abbott Pharmaceutical, Abbott Park, IL.
15	EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
16	Product Information. Ubrelvy (ubrogepant). Allergan Inc, Irvine, CA.
17	Product Information. Venclexta (venetoclax). AbbVie US LLC, North Chicago, IL.
18	Jerntorp P, Almer LO "Chlorpropamide-alcohol flushing in relation to macroangiopathy and peripheral neuropathy in non-insulin dependent diabetes." Acta Med Scand 656 (1981): 33-6. [PMID: 6953748]
19	Skillman TG, Feldman JM "The pharmacology of sulfonylureas." Am J Med 70 (1981): 361-72. [PMID: 6781341]
20	Product Information. Nexletol (bempedoic acid). Esperion Therapeutics, Ann Arbor, MI.
21	Product Information. Yupelri (revefenacin). Mylan Specialty, Morgantown, WV.
22	Product Information. Nurtec ODT (rimegepant). Biohaven Pharmaceuticals, New Haven, CT.
23	Product Information. Talzenna (talazoparib). Pfizer U.S. Pharmaceuticals Group, New York, NY.

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