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Chemistry

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Also known as: 133107-64-9, Insulin lispro (5.97 mg), Insulin-lispro, Dtxsid90157956
Molecular Formula
C257H389N65O77S6
Molecular Weight
5814  g/mol
InChI Key
WNRQPCUGRUFHED-DETKDSODSA-N

Insulin Lispro
Insulin that has been modified so that the B-chain contains a LYSINE at position 28 instead of a PROLINE and a PROLINE at position 29 instead of a LYSINE. It is used to manage BLOOD GLUCOSE levels in patients with TYPE 2 DIABETES.
1 2D Structure

Insulin Lispro

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4S)-4-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2R)-2-[[(2R)-2-[[(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]-3-sulfanylpropanoyl]amino]-3-sulfanylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl]amino]-4-methylpentanoyl]amino]-5-[[(2S)-4-amino-1-[[(2S)-1-[[(2R)-1-[[(1S)-3-amino-1-carboxy-3-oxopropyl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-5-oxopentanoic acid;(4S)-4-[[2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2R)-2-[[(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-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-4-carboxybutanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-3-sulfanylpropanoyl]amino]acetyl]amino]-5-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-6-amino-1-[(2S)-2-[[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl]pyrrolidin-1-yl]-1-oxohexan-2-yl]amino]-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
2.1.2 InChI
InChI=1S/C158H234N40O42S2.C99H155N25O35S4/c1-79(2)57-104(181-131(213)86(15)173-136(218)102(50-53-125(211)212)179-152(234)127(84(11)12)194-148(230)107(60-82(7)8)184-145(227)113(67-95-70-166-78-172-95)189-150(232)115(74-199)176-123(208)73-170-134(216)116(75-241)191-140(222)105(58-80(3)4)182-144(226)112(66-94-69-165-77-171-94)188-138(220)101(48-51-119(161)204)178-146(228)114(68-120(162)205)190-153(235)126(83(9)10)193-132(214)98(160)61-89-31-21-18-22-32-89)139(221)185-110(64-92-40-44-96(202)45-41-92)142(224)183-106(59-81(5)6)147(229)195-128(85(13)14)154(236)192-117(76-242)135(217)169-71-121(206)174-100(49-52-124(209)210)137(219)177-99(38-29-55-167-158(163)164)133(215)168-72-122(207)175-108(62-90-33-23-19-24-34-90)141(223)186-109(63-91-35-25-20-26-36-91)143(225)187-111(65-93-42-46-97(203)47-43-93)149(231)196-129(87(16)200)155(237)180-103(37-27-28-54-159)156(238)198-56-30-39-118(198)151(233)197-130(88(17)201)157(239)240;1-12-46(9)77(121-73(134)36-100)97(156)122-76(45(7)8)95(154)108-56(25-29-75(137)138)80(139)105-54(23-27-70(102)131)83(142)117-66(40-161)93(152)119-68(42-163)94(153)124-79(48(11)127)98(157)116-64(38-126)90(149)123-78(47(10)13-2)96(155)120-67(41-162)92(151)115-63(37-125)89(148)110-58(31-44(5)6)85(144)111-59(32-49-14-18-51(128)19-15-49)86(145)106-53(22-26-69(101)130)81(140)109-57(30-43(3)4)84(143)107-55(24-28-74(135)136)82(141)113-61(34-71(103)132)88(147)112-60(33-50-16-20-52(129)21-17-50)87(146)118-65(39-160)91(150)114-62(99(158)159)35-72(104)133/h18-26,31-36,40-47,69-70,77-88,98-118,126-130,199-203,241-242H,27-30,37-39,48-68,71-76,159-160H2,1-17H3,(H2,161,204)(H2,162,205)(H,165,171)(H,166,172)(H,168,215)(H,169,217)(H,170,216)(H,173,218)(H,174,206)(H,175,207)(H,176,208)(H,177,219)(H,178,228)(H,179,234)(H,180,237)(H,181,213)(H,182,226)(H,183,224)(H,184,227)(H,185,221)(H,186,223)(H,187,225)(H,188,220)(H,189,232)(H,190,235)(H,191,222)(H,192,236)(H,193,214)(H,194,230)(H,195,229)(H,196,231)(H,197,233)(H,209,210)(H,211,212)(H,239,240)(H4,163,164,167);14-21,43-48,53-68,76-79,125-129,160-163H,12-13,22-42,100H2,1-11H3,(H2,101,130)(H2,102,131)(H2,103,132)(H2,104,133)(H,105,139)(H,106,145)(H,107,143)(H,108,154)(H,109,140)(H,110,148)(H,111,144)(H,112,147)(H,113,141)(H,114,150)(H,115,151)(H,116,157)(H,117,142)(H,118,146)(H,119,152)(H,120,155)(H,121,134)(H,122,156)(H,123,149)(H,124,153)(H,135,136)(H,137,138)(H,158,159)/t86-,87+,88+,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,126-,127-,128-,129-,130-;46-,47-,48+,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,76-,77-,78-,79-/m00/s1
2.1.3 InChI Key
WNRQPCUGRUFHED-DETKDSODSA-N
2.1.4 Canonical SMILES
CCC(C)C(C(=O)NC(C(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)N)C(=O)NC(CS)C(=O)NC(CS)C(=O)NC(C(C)O)C(=O)NC(CO)C(=O)NC(C(C)CC)C(=O)NC(CS)C(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CCC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(CC(=O)N)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CS)C(=O)NC(CC(=O)N)C(=O)O)NC(=O)CN.CC(C)CC(C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CS)C(=O)NCC(=O)NC(CCC(=O)O)C(=O)NC(CCCNC(=N)N)C(=O)NCC(=O)NC(CC2=CC=CC=C2)C(=O)NC(CC3=CC=CC=C3)C(=O)NC(CC4=CC=C(C=C4)O)C(=O)NC(C(C)O)C(=O)NC(CCCCN)C(=O)N5CCCC5C(=O)NC(C(C)O)C(=O)O)NC(=O)C(C)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC6=CN=CN6)NC(=O)C(CO)NC(=O)CNC(=O)C(CS)NC(=O)C(CC(C)C)NC(=O)C(CC7=CN=CN7)NC(=O)C(CCC(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(C(C)C)NC(=O)C(CC8=CC=CC=C8)N
2.1.5 Isomeric SMILES
CC[C@H](C)[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CS)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CS)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)CN.C[C@H]([C@@H](C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)O)C(=O)O)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](CC4=CC=CC=C4)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC5=CC=C(C=C5)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC6=CN=CN6)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC7=CN=CN7)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](CC8=CC=CC=C8)N)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 28(b)-lys-29(b)-pro-insulin

2. 28(b)-lysine-29(b)-prolineinsulin

3. Humalog

4. Humalog Kwikpen

5. Insulin, Lys(28b)-pro(29b)-

6. Insulin, Lysyl(28b)-prolyl(28b)-

7. Kwikpen, Humalog

8. Lispro

9. Lispro, Insulin

10. Lyspro

2.2.2 Depositor-Supplied Synonyms

1. 133107-64-9

2. Insulin Lispro (5.97 Mg)

3. Insulin-lispro

4. Dtxsid90157956

2.3 Create Date
2007-07-03
3 Chemical and Physical Properties
Molecular Weight 5814 g/mol
Molecular Formula C257H389N65O77S6
Hydrogen Bond Donor Count84
Hydrogen Bond Acceptor Count89
Rotatable Bond Count185
Exact Mass5811.6913101 g/mol
Monoisotopic Mass5809.6846004 g/mol
Topological Polar Surface Area2310 Ų
Heavy Atom Count405
Formal Charge0
Complexity13000
Isotope Atom Count0
Defined Atom Stereocenter Count52
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameHumalog
PubMed HealthInsulin Lispro
Drug ClassesAntidiabetic
Drug LabelHumalog Mix50/50 [50% insulin lispro protamine suspension and 50% insulin lispro injection, (rDNA origin)] is a mixture of insulin lispro solution, a rapid-acting blood glucose-lowering agent and insulin lispro protamine suspension, an intermedi...
Active IngredientInsulin lispro recombinant
Dosage FormInjectable
RouteInjection
Strength100 units/ml
Market StatusPrescription
CompanyLilly

2 of 2  
Drug NameHumalog
PubMed HealthInsulin Lispro
Drug ClassesAntidiabetic
Drug LabelHumalog Mix50/50 [50% insulin lispro protamine suspension and 50% insulin lispro injection, (rDNA origin)] is a mixture of insulin lispro solution, a rapid-acting blood glucose-lowering agent and insulin lispro protamine suspension, an intermedi...
Active IngredientInsulin lispro recombinant
Dosage FormInjectable
RouteInjection
Strength100 units/ml
Market StatusPrescription
CompanyLilly

4.2 Drug Indication

Insulin lispro is indicated to improve glycemic control in adults and children with diabetes mellitus.


FDA Label


Treatment of diabetes mellitus in adults.


For the treatment of adults and children with diabetes mellitus who require insulin for the maintenance of normal glucose homeostasis. Insulin lispro Sanofi is also indicated for the initial stabilisation of diabetes mellitus.


For the treatment of adults and children with diabetes mellitus who require insulin for the maintenance of normal glucose homeostasis. Liprolog is also indicated for the initial stabilisation of diabetes mellitus.


For the treatment of adults and children with diabetes mellitus who require insulin for the maintenance of normal glucose homeostasis. Humalog is also indicated for the initial stabilisation of diabetes mellitus.


For the treatment of patients with diabetes mellitus who require insulin for the maintenance of normal glucose homeostasis. Liprolog is also indicated for the initial stabilization of diabetes mellitus. Liprolog is a short acting insulin and may be used in conjunction with a longer acting human insulin. Liprolog is indicated for preprandial administration.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Insulin is a natural hormone produced by beta cells of the pancreas. In non-diabetic individuals, a basal level of insulin is supplemented with insulin spikes following meals. Increased insulin secretion following meals is responsible for the metabolic changes that occur as the body transitions from a postabsorptive to absorptive state. Insulin promotes cellular uptake of glucose, particularly in muscle and adipose tissues, promotes energy storage via glycogenesis, opposes catabolism of energy stores, increases DNA replication and protein synthesis by stimulating amino acid uptake by liver, muscle and adipose tissue, and modifies the activity of numerous enzymes involved in glycogen synthesis and glycolysis. Insulin also promotes growth and is required for the actions of growth hormone (e.g. protein synthesis, cell division, DNA synthesis). Insulin lispro is a rapid-acting insulin analogue used to mimic postprandial insulin spikes in diabetic individuals. The onset of action of insulin lispro is 10-15 minutes. Its activity peaks 60 minutes following subcutaneous injection and its duration of action is 4-5 hours. Compared to regular human insulin, insulin lispro has a more rapid onset of action and a shorter duration of action. Insulin lispro is also shown to be equipotent to human insulin on a molar basis.


5.2 MeSH Pharmacological Classification

Hypoglycemic Agents

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Insulin [Chemical/Ingredient]; Insulin Analog [EPC]
5.4 ATC Code

A10AB04


A10AB04


A10AB04, A10AD04


A10AB04, A10AD04


A10AB04


A - Alimentary tract and metabolism

A10 - Drugs used in diabetes

A10A - Insulins and analogues

A10AB - Insulins and analogues for injection, fast-acting

A10AB04 - Insulin lispro


A - Alimentary tract and metabolism

A10 - Drugs used in diabetes

A10A - Insulins and analogues

A10AC - Insulins and analogues for injection, intermediate-acting

A10AC04 - Insulin lispro


A - Alimentary tract and metabolism

A10 - Drugs used in diabetes

A10A - Insulins and analogues

A10AD - Insulins and analogues for injection, intermediate- or long-acting combined with fast-acting

A10AD04 - Insulin lispro


5.5 Absorption, Distribution and Excretion

Absorption

Insulin lispro is rapidly absorbed following subcutaneous administration. It is also absorbed more quickly than regular human insulin. Peak serum levels occur 30-90 minutes after injection in healthy subjects. Absorption also differs depending on the site of injection. After insulin lispro was administered in the abdomen, serum drug levels were higher and the duration of action was slightly shorter than after deltoid or thigh administration. The absolute bioavailability after subcutaneous injection ranges from 55% to 77% with doses between 0.1 to 0.2 unit/kg, inclusive. The mean observed area under the serum insulin concentration-time curve from time zero to infinity was 2360 pmol hr/L and 2390 pmol hr/L for HUMALOG U-200 and HUMALOG U-100, respectively. The corresponding mean peak serum insulin concentration was 795 pmol/L and 909 pmol/L for HUMALOG U-200 and HUMALOG U-100, respectively. The median time to maximum concentration was 1.0 hour for both formulations.


Volume of Distribution

When administered intravenously as bolus injections of 0.1 and 0.2 U/kg dose in two separate groups of healthy subjects, the mean volume of distribution of insulin lispro appeared to decrease with increase in dose (1.55 and 0.72 L/kg, respectively).


Clearance

Clearance is dose dependent. When a dose of 0.1 unit/kg and 0.2 unit/kg were administered intravenously, the mean clearance was 21.0 mL/min/kg and 9.6 mL/min/kg respectively.


5.6 Metabolism/Metabolites

Insulin is predominantly cleared by metabolic degradation via a receptor-mediated process.


5.7 Biological Half-Life

After subcutaneous administration of insulin lispro, the t1/2 is shorter than that of regular human insulin (1 versus 1.5 hours, respectively).


5.8 Mechanism of Action

Insulin lispro binds to the insulin receptor (IR), a heterotetrameric protein consisting of two extracellular alpha units and two transmembrane beta units. The binding of insulin to the alpha subunit of IR stimulates the tyrosine kinase activity intrinsic to the beta subunit of the receptor. The bound receptor autophosphorylates and phosphorylates numerous intracellular substrates such as insulin receptor substrates (IRS) proteins, Cbl, APS, Shc and Gab 1. Activation of these proteins leads to the activation of downstream signaling molecules including PI3 kinase and Akt. Akt regulates the activity of glucose transporter 4 (GLUT4) and protein kinase C (PKC), both of which play critical roles in metabolism and catabolism. In humans, insulin is stored in the form of hexamers; however, only insulin monomers are able to interact with IR. Reversal of the proline and lysine residues at positions B28 and B29 of native insulin eliminates hydrophobic interactions and weakens some of the hydrogen bonds that contribute to the stability of the insulin dimers that comprise insulin hexamers. Hexamers of insulin lispro are produced in the presence of zinc and m-cresol. These weakly associated hexamers quickly dissociate upon subcutaneous injection and are absorbed as monomers through vascular endothelial cells. These properties give insulin lispro its fast-acting properties.


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