Details of the Drug

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], [2]
Malaria	1F40-1F45	Phase 3	[3]
Type-1 diabetes	5A10	Phase 3	[4], [5]
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

Topological Polar Surface Area (xlogp)

-14.1

Rotatable Bond Count (rotbonds)

191

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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

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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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]	[11]
Oxymetholone	DMFXUT8	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Oxymetholone.	Aplastic anaemia [3A70]	[11]
Sulfamethoxazole	DMB08GE	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfamethoxazole.	Bacterial infection [1A00-1C4Z]	[11]
Linezolid	DMGFPU2	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Linezolid.	Bacterial infection [1A00-1C4Z]	[11]
Fluoxymesterone	DMUHCF1	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Fluoxymesterone.	Breast cancer [2C60-2C6Y]	[11]
Fenofibric acid	DMGO2MC	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Fenofibric acid.	Cardiovascular disease [BA00-BE2Z]	[11]
Sertraline	DM0FB1J	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Sertraline.	Depression [6A70-6A7Z]	[11]
Fluoxetine	DM3PD2C	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Fluoxetine.	Depression [6A70-6A7Z]	[11]
Vilazodone	DM4LECQ	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Vilazodone.	Depression [6A70-6A7Z]	[11]
Paroxetine	DM5PVQE	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Paroxetine.	Depression [6A70-6A7Z]	[11]
Selegiline	DM6034S	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Selegiline.	Depression [6A70-6A7Z]	[11]
Vortioxetine	DM6F1PU	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Vortioxetine.	Depression [6A70-6A7Z]	[11]
Isocarboxazid	DMAF1NB	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Isocarboxazid.	Depression [6A70-6A7Z]	[11]
Escitalopram	DMFK9HG	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Escitalopram.	Depression [6A70-6A7Z]	[11]
Tranylcypromine	DMGB5RE	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Tranylcypromine.	Depression [6A70-6A7Z]	[11]
Phenelzine	DMHIDUE	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Phenelzine.	Depression [6A70-6A7Z]	[11]
Fluvoxamine	DMQTJSX	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Fluvoxamine.	Depression [6A70-6A7Z]	[11]
PMID28454500-Compound-96	DM2A75P	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and PMID28454500-Compound-96.	Discovery agent [N.A.]	[11]
Citalopram derivative 1	DMITX1G	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Citalopram derivative 1.	Discovery agent [N.A.]	[11]
PMID28870136-Compound-49	DMTUC9E	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and PMID28870136-Compound-49.	Discovery agent [N.A.]	[11]
Sunitinib	DMCBJSR	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Sunitinib.	Gastrointestinal stromal tumour [2B5B]	[11]
Ramipril	DM2R68E	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Ramipril.	Heart failure [BD10-BD1Z]	[11]
Gemfibrozil	DMD8Q3J	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Gemfibrozil.	Hyper-lipoproteinaemia [5C80]	[11]
Fenofibrate	DMFKXDY	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Fenofibrate.	Hyper-lipoproteinaemia [5C80]	[11]
Clofibrate	DMPC1J7	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Clofibrate.	Hyper-lipoproteinaemia [5C80]	[11]
Eprosartan	DM07K2I	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Eprosartan.	Hypertension [BA00-BA04]	[11]
Moexipril	DM26E4B	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Moexipril.	Hypertension [BA00-BA04]	[11]
Captopril	DM458UM	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Captopril.	Hypertension [BA00-BA04]	[11]
Trandolapril	DM4L6EU	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Trandolapril.	Hypertension [BA00-BA04]	[11]
Losartan	DM72JXH	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Losartan.	Hypertension [BA00-BA04]	[11]
Fosinopril	DM9NJ52	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Fosinopril.	Hypertension [BA00-BA04]	[11]
TAK-491	DMCF6SX	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and TAK-491.	Hypertension [BA00-BA04]	[11]
Benazepril	DMH1M9B	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Benazepril.	Hypertension [BA00-BA04]	[11]
Enalapril	DMNFUZR	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Enalapril.	Hypertension [BA00-BA04]	[11]
Perindopril	DMOPZDT	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Perindopril.	Hypertension [BA00-BA04]	[11]
Quinapril	DMR8H31	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Quinapril.	Hypertension [BA00-BA04]	[11]
Telmisartan	DMS3GX2	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Telmisartan.	Hypertension [BA00-BA04]	[11]
Irbesartan	DMTP1DC	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Irbesartan.	Hypertension [BA00-BA04]	[11]
Lisinopril	DMUOK4C	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Lisinopril.	Hypertension [BA00-BA04]	[11]
Testosterone	DM7HUNW	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Testosterone.	Low bone mass disorder [FB83]	[11]
Chloroquine	DMSI5CB	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Chloroquine.	Malaria [1F40-1F45]	[11]
Hydroxychloroquine	DMSIVND	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Hydroxychloroquine.	Malaria [1F40-1F45]	[11]
Quinine	DMSWYF5	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Quinine.	Malaria [1F40-1F45]	[11]
Sulphadoxine	DMZI2UF	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulphadoxine.	Malaria [1F40-1F45]	[11]
Mecasermin	DM1O3BY	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Mecasermin.	Multiple structural anomalies syndrome [LD2F]	[11]
Dextropropoxyphene	DM23HCX	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Dextropropoxyphene.	Pain [MG30-MG3Z]	[12]
Aspirin	DM672AH	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Aspirin.	Pain [MG30-MG3Z]	[12]
Diflunisal	DM7EN8I	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Diflunisal.	Pain [MG30-MG3Z]	[11]
Safinamide	DM0YWJC	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Safinamide.	Parkinsonism [8A00]	[11]
Rasagiline	DM3WKQ4	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Rasagiline.	Parkinsonism [8A00]	[11]
Choline salicylate	DM8P137	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Choline salicylate.	Postoperative inflammation [1A00-CA43]	[11]
Sulfadiazine	DMTW3R8	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfadiazine.	Rheumatic fever [1B40]	[11]
Salsalate	DM13P4C	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Salsalate.	Rheumatoid arthritis [FA20]	[11]
Sulfasalazine	DMICA9H	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfasalazine.	Rheumatoid arthritis [FA20]	[11]
Salicyclic acid	DM2F8XZ	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Salicyclic acid.	Seborrhoeic dermatitis [EA81]	[12]
Methyltestosterone	DMWLFGO	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Methyltestosterone.	Solid tumour/cancer [2A00-2F9Z]	[11]
Sulfamethizole	DMGCHDS	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfamethizole.	Urinary tract infection [GC08]	[11]
Sulfisoxazole	DMXLT8C	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Sulfisoxazole.	Urinary tract infection [GC08]	[11]
Disopyramide	DM5SYZP	Moderate	Increased risk of hypoglycemia by the combination of Insulin-glargine and Disopyramide.	Ventricular tachyarrhythmia [BC71]	[11]
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⏷ 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	Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
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)
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8	Radium 223 dichloride for prostate cancer treatment. Drug Des Devel Ther. 2017 Sep 6;11:2643-2651.
9	Efficacy and safety of LY2963016 insulin glargine compared with insulin glargine (Lantus ) in patients with type 1 diabetes in a randomized controlled trial: the ELEMENT 1 study. Diabetes Obes Metab.2015 Aug;17(8):726-33.
10	Biosimilar insulins: a European perspective. Diabetes Obes Metab. 2015 May; 17(5): 445-451.
11	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]
12	Asplund K, Wiholm BE, Lithner F "Glibenclamide-associated hypoglycaemia: a report on 57 cases." Diabetologia 24 (1983): 412-7. [PMID: 6411511]