General Information of Drug (ID: DMR4HIW)

Drug Name
Insulin-glargine
Synonyms Glargine; Lantus; SoloStar; SoloStar [Insulin delivery pen]; A21-Gly-B31-Arg-B32-Arg-insulin
Indication
Disease Entry ICD 11 Status REF
Diabetic complication 5A2Y Approved [1]
Non-insulin dependent diabetes 5A11 Approved [2]
Malaria 1F40-1F45 Phase 3 [3]
Type-1 diabetes 5A10 Phase 3 [4]
Type-2 diabetes 5A11 Application submitted [5]
Therapeutic Class
Hypoglycemic Agents
Drug Type
Small molecular drug
Sequence
>A chain
GIVEQCCTSICSLYQLENYCG
>B chain
FVNQHLCGSHLVEALYLVCGERGFFYTPKTRR
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 5 Molecular Weight (mw) 6063
Logarithm of the Partition Coefficient (xlogp) -14.1
Rotatable Bond Count (rotbonds) 191
Hydrogen Bond Donor Count (hbonddonor) 85
Hydrogen Bond Acceptor Count (hbondacc) 92
Chemical Identifiers
Formula
C267H404N72O78S6
IUPAC Name
(4S)-4-[[2-[[(1R,6R,12S,15S,18S,21S,24S,27S,30S,33S,36S,39S,42R,47R,50S,53S,56S,59S,62S,65S,68S,71S,74R,77S,80S,83S,88R)-88-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[(2-aminoacetyl)amino]-3-methylpentanoyl]amino]-3-methylbutanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]-6-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-methylbutanoyl]amino]-4-oxobutanoyl]amino]-5-oxopentanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-4-methylpentanoyl]amino]-53-(2-amino-2-oxoethyl)-62-(3-amino-3-oxopropyl)-77-[(2S)-butan-2-yl]-24,56-bis(2-carboxyethyl)-47-(carboxymethylcarbamoyl)-83-[(1R)-1-hydroxyethyl]-12,71,80-tris(hydroxymethyl)-33,50,65-tris[(4-hydroxyphenyl)methyl]-15-(1H-imidazol-4-ylmethyl)-27-methyl-18,30,36,59,68-pentakis(2-methylpropyl)-7,10,13,16,19,22,25,28,31,34,37,40,49,52,55,58,61,64,67,70,73,76,79,82,85,87-hexacosaoxo-21,39-di(propan-2-yl)-3,4,44,45,90,91-hexathia-8,11,14,17,20,23,26,29,32,35,38,41,48,51,54,57,60,63,66,69,72,75,78,81,84,86-hexacosazabicyclo[72.11.7]dononacontane-42-carbonyl]amino]acetyl]amino]-5-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[(2S)-2-[[(2S)-6-amino-1-[[(2S,3R)-1-[[(2S)-5-carbamimidamido-1-[[(1S)-4-carbamimidamido-1-carboxybutyl]amino]-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
Canonical SMILES
CC[C@H](C)[C@H]1C(=O)N[C@H]2CSSC[C@@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC2=O)CO)CC(C)C)CC3=CC=C(C=C3)O)CCC(=O)N)CC(C)C)CCC(=O)O)CC(=O)N)CC4=CC=C(C=C4)O)C(=O)NCC(=O)O)C(=O)NCC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](CC5=CC=CC=C5)C(=O)N[C@@H](CC6=CC=CC=C6)C(=O)N[C@@H](CC7=CC=C(C=C7)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N8CCC[C@H]8C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)C(C)C)CC(C)C)CC9=CC=C(C=C9)O)CC(C)C)C)CCC(=O)O)C(C)C)CC(C)C)CC2=CNC=N2)CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC2=CNC=N2)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC2=CC=CC=C2)N)C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CO)[C@@H](C)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)CN
InChI
InChI=1S/C267H404N72O78S6/c1-29-137(23)212(330-199(355)109-269)260(412)334-211(136(21)22)256(408)305-166(79-86-206(365)366)226(378)298-163(75-82-196(273)352)230(382)326-190-122-421-422-123-191-251(403)322-185(117-341)249(401)312-170(94-129(7)8)234(386)313-176(101-146-57-65-152(346)66-58-146)237(389)299-161(73-80-194(271)350)227(379)308-169(93-128(5)6)232(384)301-165(78-85-205(363)364)229(381)320-182(107-197(274)353)244(396)316-178(103-148-61-69-154(348)70-62-148)240(392)325-188(222(374)290-115-207(367)368)120-418-420-121-189(221(373)288-112-200(356)294-160(76-83-203(359)360)225(377)297-157(53-42-88-284-265(276)277)219(371)287-113-201(357)295-174(99-144-48-36-32-37-49-144)236(388)315-175(100-145-50-38-33-39-51-145)239(391)317-179(104-149-63-71-155(349)72-64-149)247(399)338-216(142(28)345)263(415)339-91-45-56-193(339)254(406)302-158(52-40-41-87-268)231(383)336-214(140(26)343)261(413)303-159(54-43-89-285-266(278)279)224(376)306-167(264(416)417)55-44-90-286-267(280)281)328-258(410)210(135(19)20)333-245(397)172(96-131(11)12)310-238(390)177(102-147-59-67-153(347)68-60-147)314-233(385)168(92-127(3)4)307-217(369)139(25)293-223(375)164(77-84-204(361)362)304-255(407)209(134(17)18)332-246(398)173(97-132(13)14)311-242(394)181(106-151-111-283-126-292-151)319-248(400)184(116-340)296-202(358)114-289-220(372)187(119-419-423-124-192(327-252(190)404)253(405)337-215(141(27)344)262(414)323-186(118-342)250(402)335-213(138(24)30-2)259(411)329-191)324-235(387)171(95-130(9)10)309-241(393)180(105-150-110-282-125-291-150)318-228(380)162(74-81-195(272)351)300-243(395)183(108-198(275)354)321-257(409)208(133(15)16)331-218(370)156(270)98-143-46-34-31-35-47-143/h31-39,46-51,57-72,110-111,125-142,156-193,208-216,340-349H,29-30,40-45,52-56,73-109,112-124,268-270H2,1-28H3,(H2,271,350)(H2,272,351)(H2,273,352)(H2,274,353)(H2,275,354)(H,282,291)(H,283,292)(H,287,371)(H,288,373)(H,289,372)(H,290,374)(H,293,375)(H,294,356)(H,295,357)(H,296,358)(H,297,377)(H,298,378)(H,299,389)(H,300,395)(H,301,384)(H,302,406)(H,303,413)(H,304,407)(H,305,408)(H,306,376)(H,307,369)(H,308,379)(H,309,393)(H,310,390)(H,311,394)(H,312,401)(H,313,386)(H,314,385)(H,315,388)(H,316,396)(H,317,391)(H,318,380)(H,319,400)(H,320,381)(H,321,409)(H,322,403)(H,323,414)(H,324,387)(H,325,392)(H,326,382)(H,327,404)(H,328,410)(H,329,411)(H,330,355)(H,331,370)(H,332,398)(H,333,397)(H,334,412)(H,335,402)(H,336,383)(H,337,405)(H,338,399)(H,359,360)(H,361,362)(H,363,364)(H,365,366)(H,367,368)(H,416,417)(H4,276,277,284)(H4,278,279,285)(H4,280,281,286)/t137-,138-,139-,140+,141+,142+,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,180-,181-,182-,183-,184-,185-,186-,187-,188-,189-,190-,191-,192-,193-,208-,209-,210-,211-,212-,213-,214-,215-,216-/m0/s1
InChIKey
COCFEDIXXNGUNL-RFKWWTKHSA-N
Cross-matching ID
PubChem CID
118984454
CAS Number
160337-95-1
TTD ID
D07NGZ
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Insulin (INS) TTZOPHG INS_HUMAN Modulator [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Insulin receptor (INSR) OTTY341H INSR_HUMAN Post-Translational Modifications [7]
Insulin-like growth factor 1 receptor (IGF1R) OTXJIF13 IGF1R_HUMAN Post-Translational Modifications [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Diabetic complication
ICD Disease Classification 5A2Y
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Insulin (INS) DTT INS 6.70E-01 -0.12 -0.46
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Insulin-glargine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Oxandrolone DMU9MYJ Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Oxandrolone. Alcoholic liver disease [DB94] [8]
Oxymetholone DMFXUT8 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Oxymetholone. Aplastic anaemia [3A70] [8]
Sulfamethoxazole DMB08GE Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfamethoxazole. Bacterial infection [1A00-1C4Z] [8]
Linezolid DMGFPU2 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Linezolid. Bacterial infection [1A00-1C4Z] [8]
Fluoxymesterone DMUHCF1 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Fluoxymesterone. Breast cancer [2C60-2C6Y] [8]
Fenofibric acid DMGO2MC Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Fenofibric acid. Cardiovascular disease [BA00-BE2Z] [8]
Sertraline DM0FB1J Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Sertraline. Depression [6A70-6A7Z] [8]
Fluoxetine DM3PD2C Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Fluoxetine. Depression [6A70-6A7Z] [8]
Vilazodone DM4LECQ Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Vilazodone. Depression [6A70-6A7Z] [8]
Paroxetine DM5PVQE Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Paroxetine. Depression [6A70-6A7Z] [8]
Selegiline DM6034S Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Selegiline. Depression [6A70-6A7Z] [8]
Vortioxetine DM6F1PU Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Vortioxetine. Depression [6A70-6A7Z] [8]
Isocarboxazid DMAF1NB Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Isocarboxazid. Depression [6A70-6A7Z] [8]
Escitalopram DMFK9HG Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Escitalopram. Depression [6A70-6A7Z] [8]
Tranylcypromine DMGB5RE Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Tranylcypromine. Depression [6A70-6A7Z] [8]
Phenelzine DMHIDUE Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Phenelzine. Depression [6A70-6A7Z] [8]
Fluvoxamine DMQTJSX Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Fluvoxamine. Depression [6A70-6A7Z] [8]
PMID28454500-Compound-96 DM2A75P Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and PMID28454500-Compound-96. Discovery agent [N.A.] [8]
Citalopram derivative 1 DMITX1G Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Citalopram derivative 1. Discovery agent [N.A.] [8]
PMID28870136-Compound-49 DMTUC9E Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and PMID28870136-Compound-49. Discovery agent [N.A.] [8]
Sunitinib DMCBJSR Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Sunitinib. Gastrointestinal stromal tumour [2B5B] [8]
Ramipril DM2R68E Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Ramipril. Heart failure [BD10-BD1Z] [8]
Gemfibrozil DMD8Q3J Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Gemfibrozil. Hyper-lipoproteinaemia [5C80] [8]
Fenofibrate DMFKXDY Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Fenofibrate. Hyper-lipoproteinaemia [5C80] [8]
Clofibrate DMPC1J7 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Clofibrate. Hyper-lipoproteinaemia [5C80] [8]
Eprosartan DM07K2I Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Eprosartan. Hypertension [BA00-BA04] [8]
Moexipril DM26E4B Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Moexipril. Hypertension [BA00-BA04] [8]
Captopril DM458UM Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Captopril. Hypertension [BA00-BA04] [8]
Trandolapril DM4L6EU Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Trandolapril. Hypertension [BA00-BA04] [8]
Losartan DM72JXH Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Losartan. Hypertension [BA00-BA04] [8]
Fosinopril DM9NJ52 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Fosinopril. Hypertension [BA00-BA04] [8]
TAK-491 DMCF6SX Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and TAK-491. Hypertension [BA00-BA04] [8]
Benazepril DMH1M9B Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Benazepril. Hypertension [BA00-BA04] [8]
Enalapril DMNFUZR Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Enalapril. Hypertension [BA00-BA04] [8]
Perindopril DMOPZDT Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Perindopril. Hypertension [BA00-BA04] [8]
Quinapril DMR8H31 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Quinapril. Hypertension [BA00-BA04] [8]
Telmisartan DMS3GX2 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Telmisartan. Hypertension [BA00-BA04] [8]
Irbesartan DMTP1DC Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Irbesartan. Hypertension [BA00-BA04] [8]
Lisinopril DMUOK4C Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Lisinopril. Hypertension [BA00-BA04] [8]
Testosterone DM7HUNW Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Testosterone. Low bone mass disorder [FB83] [8]
Chloroquine DMSI5CB Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Chloroquine. Malaria [1F40-1F45] [8]
Hydroxychloroquine DMSIVND Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Hydroxychloroquine. Malaria [1F40-1F45] [8]
Quinine DMSWYF5 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Quinine. Malaria [1F40-1F45] [8]
Sulphadoxine DMZI2UF Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulphadoxine. Malaria [1F40-1F45] [8]
Mecasermin DM1O3BY Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Mecasermin. Multiple structural anomalies syndrome [LD2F] [8]
Dextropropoxyphene DM23HCX Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Dextropropoxyphene. Pain [MG30-MG3Z] [9]
Aspirin DM672AH Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Aspirin. Pain [MG30-MG3Z] [9]
Diflunisal DM7EN8I Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Diflunisal. Pain [MG30-MG3Z] [8]
Safinamide DM0YWJC Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Safinamide. Parkinsonism [8A00] [8]
Rasagiline DM3WKQ4 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Rasagiline. Parkinsonism [8A00] [8]
Choline salicylate DM8P137 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Choline salicylate. Postoperative inflammation [1A00-CA43] [8]
Sulfadiazine DMTW3R8 Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfadiazine. Rheumatic fever [1B40] [8]
Salsalate DM13P4C Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Salsalate. Rheumatoid arthritis [FA20] [8]
Sulfasalazine DMICA9H Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfasalazine. Rheumatoid arthritis [FA20] [8]
Salicyclic acid DM2F8XZ Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Salicyclic acid. Seborrhoeic dermatitis [EA81] [9]
Methyltestosterone DMWLFGO Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Methyltestosterone. Solid tumour/cancer [2A00-2F9Z] [8]
Sulfamethizole DMGCHDS Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfamethizole. Urinary tract infection [GC08] [8]
Sulfisoxazole DMXLT8C Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfisoxazole. Urinary tract infection [GC08] [8]
Disopyramide DM5SYZP Moderate Increased risk of hypoglycemia by the combination of Insulin-glargine and Disopyramide. Ventricular tachyarrhythmia [BC71] [8]
⏷ Show the Full List of 59 DDI Information of This Drug

References

1 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: 7572).
2 Effect of Subcutaneous Tirzepatide vs Placebo Added to Titrated Insulin Glargine on Glycemic Control in Patients With Type 2 Diabetes: The SURPASS-5 Randomized Clinical Trial. JAMA. 2022 Feb 8;327(6):534-545.
3 ClinicalTrials.gov (NCT02059161) A Study of the Safety and Efficacy of MK-1293 Compared to Lantus in Participants With Type 1 Diabetes Mellitus (T1DM) (MK-1293-003). U.S. National Institutes of Health.
4 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
5 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
6 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
7 IR and IGF-1R expression affects insulin induced proliferation and DNA damage. Toxicol In Vitro. 2017 Mar;39:68-74. doi: 10.1016/j.tiv.2016.11.011. Epub 2016 Nov 22.
8 Abad S, Moachon L, Blanche P, Bavoux F, Sicard D, Salmon-Ceron D "Possible interaction between glicazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia." Br J Clin Pharmacol 52 (2001): 456-7. [PMID: 11678792]
9 Asplund K, Wiholm BE, Lithner F "Glibenclamide-associated hypoglycaemia: a report on 57 cases." Diabetologia 24 (1983): 412-7. [PMID: 6411511]