Insulin detemir

Identification

Summary

Insulin detemir is a long-acting form of insulin used for glycemic control in type 1 and type 2 diabetes mellitus.

Brand Names

Levemir

Generic Name

Insulin detemir

DrugBank Accession Number

DB01307

Background

Insulin detemir is a long-acting form of insulin used for the treatment of hyperglycemia caused by Type 1 and Type 2 Diabetes.^1,2,3,5 Insulin is typically prescribed for the management of diabetes mellitus to mimic the activity of endogenously produced human insulin, a peptide hormone produced by beta cells of the pancreas that promotes glucose metabolism.^1,2,3,5 Insulin is released from the pancreas following a meal to promote the uptake of glucose from the blood into internal organs and tissues such as the liver, fat cells, and skeletal muscle.^1,2,3,5 The absorption of glucose into cells allows for its transformation into glycogen or fat for storage.^1,2,3,5 Insulin also inhibits hepatic glucose production, enhances protein synthesis, and inhibits lipolysis and proteolysis among many other functions.^1,2,3,5

Insulin is an important treatment in the management of Type 1 Diabetes (T1D) which is caused by an autoimmune reaction that destroys the beta cells of the pancreas, resulting in the body not being able to produce or synthesize the insulin needed to manage circulating blood sugar levels.^1,2,3,5 As a result, people with T1D rely primarily on exogenous forms of insulin, such as insulin detemir, to lower glucose levels in the blood.^1,2,3,5 Insulin is also used in the treatment of Type 2 Diabetes (T2D), another form of diabetes mellitus that is a slowly progressing metabolic disorder caused by a combination of genetic and lifestyle factors that promote chronically elevated blood sugar levels.^1,2,3,5 Without treatment or improvement in non-pharmacological measures such as diet and exercise to lower blood glucose, high blood sugar eventually causes cellular resistance to endogenous insulin, and in the long term, damage to pancreatic islet cells.^1,2,3,5 Insulin is typically prescribed later in the course of T2D, after several oral medications such as Metformin, Gliclazide, or Sitagliptin have been tried, when sufficient damage has been caused to pancreatic cells that the body is no longer able to produce insulin on its own.^1,2,3,5

Marketed as the brand name product Levemir, insulin detemir has a duration of action of 16-24 hours allowing for once-daily dosing, typically at bedtime.^1,2,3,5 Due to its duration of action, Levemir is considered "basal insulin" as it provides low concentrations of background insulin that can keep blood sugar stable between meals or overnight.^1,2,3,5 Basal insulin is often combined with short-acting "bolus insulin" such as Insulin lispro, Insulin glulisine, and Insulin aspart to provide higher doses of insulin required following meals.^1,2,3,5 Use of basal and bolus insulin together is intended to mimic the pancreas' production of endogenous insulin, with a goal of avoiding any periods of hypoglycemia.^1,2,3,5

Insulin detemir is produced using recombinant DNA technology in yeast cells.^1,2,3,5 This insulin analogue has a 14-C fatty acid, myristic acid, bound to the lysine amino acid at position B29. The myristoyl side chain increases self-association and albumin binding.^1,2,3,5 This along with slow systemic absorption from the injection site prolongs distribution of the hormone into tissues and results in a long duration of action. ^1,2,3,5

Without an adequate supply of insulin to promote absorption of glucose from the bloodstream, blood sugar levels can climb to dangerously high levels and can result in symptoms such as fatigue, headache, blurred vision, and increased thirst.^1,2,3,5 If left untreated, the body starts to break down fat, instead of glucose, for energy which results in a build-up of ketone acids in the blood and a syndrome called ketoacidosis, which is a life-threatening medical emergency. In the long term, elevated blood sugar levels increase the risk of heart attack, stroke, and diabetic neuropathy.^1,2,3,5

Type

Biotech

Groups

Approved

Biologic Classification

Protein Based Therapies
Insulins

Protein Structure

Protein Chemical Formula

C₂₆₇H₄₀₂N₆₄O₇₆S₆

Protein Average Weight

5916.9 Da

Sequences

>Protein sequence for A chain
GIVEQCCTSICSLYQLENYCN

>Protein sequence for B chain 
FVNQHLCGSHLVEALYLVCGERGFFYTPK

Download FASTA Format

Synonyms

• Detemir
• Insulin detemir
• Insulin detemir recombinant
• Insulin,detemir,human
• Insulina detemir

External IDs

• NN-304

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Pharmacology

Indication

Insulin detemir is indicated to improve glycemic control in adults and children with diabetes mellitus.¹²

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Type 1 diabetes mellitus		••••••••••••	••••••••••• •••••• ••••••••		•••••••••• ••••••••
Management of	Type 1 insulin-dependent diabetes mellitus		••••••••••••	•••••• ••••••••		•••••••••• ••••••••
Used in combination to manage	Type 2 diabetes mellitus	Regimen in combination with: Metformin (DB00331), Liraglutide (DB06655)	••••••••••••	•••••	•••••••••• ••••••••• •••••••	•••••••••• ••••••••
Used in combination to manage	Type 2 diabetes mellitus		••••••••••••	•••••	•••••••••• ••••••••• •••••••	•••••••••• ••••••••
Management of	Type 2 diabetes mellitus		••••••••••••	•••••• •••••••••		•••••••••• ••••••••

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Pharmacodynamics

Insulin is a natural hormone produced by beta cells of the pancreas.³ In non-diabetic individuals, the pancreas produces a continuous supply of low levels of basal insulin along with spikes of insulin following meals.^3,2 Increased insulin secretion following meals is responsible for the metabolic changes that occur as the body transitions from a postabsorptive to absorptive state.^3,2 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 the liver, muscle and adipose tissue, and modifies the activity of numerous enzymes involved in glycogen synthesis and glycolysis.^3,2 Insulin also promotes growth and is required for the actions of growth hormone (e.g. protein synthesis, cell division, DNA synthesis).^3,2 Insulin detemir is a long-acting insulin analogue with a flat and predictable action profile.^3,2 It is used to mimic the basal levels of insulin in diabetic individuals. The onset of action of insulin detemir is 1 to 2 hours and its duration of action is up to 24 hours.^3,2 Interestingly, it has a lower affinity (30%) for the insulin receptor than human insulin.^3,2

Mechanism of action

Insulin detemir binds to the insulin receptor (IR), a heterotetrameric protein consisting of two extracellular alpha units and two transmembrane beta units.⁸ The binding of insulin to the alpha subunit of IR stimulates the tyrosine kinase activity intrinsic to the beta subunit of the receptor.^8,9 The bound receptor autophosphorylates and phosphorylates numerous intracellular substrates such as insulin receptor substrates (IRS) proteins, Cbl, APS, Shc and Gab 1.⁹ Activation of these proteins leads to the activation of downstream signalling molecules including PI3 kinase and Akt.⁹ Akt regulates the activity of glucose transporter 4 (GLUT4) and protein kinase C (PKC), both of which play critical roles in metabolism and catabolism.^9,10

Insulin detemir’s long duration of action appears to be a result of slow systemic absorption from the injection site and delayed distribution to target tissues.⁶ The myristic acid side chain on insulin detemir increases self-association and gives it a high binding affinity to serum albumin. These features slow its distribution into target tissues and prolong its duration of action.⁶

Target	Actions	Organism
AInsulin receptor	agonist	Humans
UInsulin-like growth factor 1 receptor	activator	Humans

Absorption

After subcutaneous injection of LEVEMIR in healthy subjects and in patients with diabetes, insulin detemir serum concentrations had a relatively constant concentration/time profile over 24 hours with the maximum serum concentration (Cmax) reached between 6-8 hours post dose.¹² When single dose of 0.5 units/kg of insulin detemir was given to adult type 1 diabetes patients, the maximum serum concentration (Cmax) was 4,641 ± 2,299 pmol/L.^12,4Insulin detemir was more slowly absorbed after subcutaneous administration to the thigh where AUC_0-5h was 30 40% lower and AUC_0-∞ was 10% lower than the corresponding AUCs with subcutaneous injections to the deltoid and abdominal regions.¹²

Insulin detemir has a slow and prolonged absorption and a relatively constant concentration/time profile over 24 hours with no pronounced peak. The median time to maximum serum insulin concentration was 12 hours after injection. On average, serum insulin concentrations declined to baseline by approximately 24 hours.^12,1

The absolute bioavailability of insulin detemir is approximately 60%.¹²

Volume of distribution

Insulin detemir has an apparent volume of distribution of approximately 0.1 L/kg.¹²

Protein binding

More than 98% of insulin detemir in the bloodstream is bound to albumin. The results of in vitro and in vivo protein binding studies demonstrate that there is no clinically relevant interaction between insulin detemir and fatty acids or other protein-bound drugs.¹²

Metabolism

The liver and kidney play the major role in metabolizing insulin.⁶However, while the liver predominantly metabolizes endogenous insulin, exogenous insulin is primarily metabolized due to the kidney since it is not directly delivered into the portal system.⁶

Route of elimination

30 to 80% of circulating insulin is removed by the kidney.⁷

Half-life

After subcutaneous administration in patients with type 1 diabetes, insulin detemir has a terminal half-life of 5 to 7 hours depending on dose.¹²

Clearance

The apparent clearance (CL/F) was fairly consistent among different patients population with type 1 diabetes. It was estimated to be 3.43 ± 1.36 L/min·kg in 6 to 12 years old patients, 3.74 ± 0.98 L/min·kg in 13 to 17 years old, and 3.41 ± 1.00 L/min·kg in adult patients (18-65 years old).⁴

Adverse Effects

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Toxicity

An excess of insulin relative to food intake, energy expenditure, or both may lead to severe and sometimes prolonged and life-threatening hypoglycemia and hypokalemia [see Warnings and Precautions (5.3, 5.6)]. Mild episodes of hypoglycemia usually can be treated with oral glucose.¹² Lowering the insulin dosage, and adjustments in meal patterns, or exercise may be needed. More severe episodes with coma, seizure, or neurologic impairment may be treated with a glucagon product for emergency use or concentrated intravenous glucose.¹² Neurogenic (autonomic) signs and symptoms of hypoglycemia include trembling, palpitations, sweating, anxiety, hunger, nausea and tingling. Neuroglycopenic signs and symptoms of hypoglycemia include difficulty concentrating, lethargy/weakness, confusion, drowsiness, vision changes, difficulty speaking, headache, and dizziness.¹²Individuals may become unconscious in severe cases of hypoglycemia. Injection site reactions may also occur. Symptoms include: redness, inflammation, bruising, swelling and itching at the injection site.¹² After apparent clinical recovery from hypoglycemia, continued observation and additional carbohydrate intake may be necessary to avoid recurrence of hypoglycemia. Hypokalemia must be corrected appropriately.¹²

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Acarbose	The risk or severity of hypoglycemia can be increased when Acarbose is combined with Insulin detemir.
Acebutolol	The therapeutic efficacy of Insulin detemir can be increased when used in combination with Acebutolol.
Acetazolamide	The risk or severity of hypoglycemia can be increased when Acetazolamide is combined with Insulin detemir.
Acetohexamide	The risk or severity of hypoglycemia can be increased when Acetohexamide is combined with Insulin detemir.
Acetophenazine	The therapeutic efficacy of Insulin detemir can be decreased when used in combination with Acetophenazine.

Food Interactions

• Avoid alcohol. Alcohol may impair blood glucose control.
• Take with food. Once daily administration should be given with the evening meal or prior to bedtime.

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International/Other Brands

Levemir FlexPen (Novo Nordisk)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Levemir	Injection, solution	100 [iU]/1mL	Subcutaneous	A-S Medication Solutions	2006-03-27	Not applicable
Levemir	Injection, solution	100 U/ml	Subcutaneous	Novo Nordisk	2016-09-08	Not applicable
Levemir	Injection	14.2 mg/1mL	Subcutaneous	Novo Nordisk Inc.	2007-08-17	2007-08-17
Levemir	Injection, solution	100 U/ml	Subcutaneous	Novo Nordisk	2016-09-08	Not applicable
Levemir	Injection, solution	100 U/ml	Subcutaneous	Novo Nordisk	2016-09-08	Not applicable

Categories

ATC Codes

A10AE05 — Insulin detemir

• A10AE — Insulins and analogues for injection, long-acting
• A10A — INSULINS AND ANALOGUES
• A10 — DRUGS USED IN DIABETES
• A — ALIMENTARY TRACT AND METABOLISM

Drug Categories

• Alimentary Tract and Metabolism
• Amino Acids, Peptides, and Proteins
• Blood Glucose Lowering Agents
• Cytochrome P-450 CYP1A2 Inducers
• Cytochrome P-450 CYP1A2 Inducers (strength unknown)
• Cytochrome P-450 Enzyme Inducers
• Drugs Used in Diabetes
• Hormones
• Hormones, Hormone Substitutes, and Hormone Antagonists
• Hypoglycemia-Associated Agents
• Insulin
• Insulin Analog
• Insulin, Long-Acting
• Pancreatic Hormones
• Peptide Hormones
• Peptides

Chemical TaxonomyProvided by Classyfire

Description

Not Available

Kingdom

Organic Compounds

Super Class

Organic Acids

Class

Carboxylic Acids and Derivatives

Sub Class

Amino Acids, Peptides, and Analogues

Direct Parent

Peptides

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

4FT78T86XV

CAS number

169148-63-4

References

General References

1. Kurtzhals P: Pharmacology of insulin detemir. Endocrinol Metab Clin North Am. 2007 Aug;36 Suppl 1:14-20. [Article]
2. Morales J: Defining the role of insulin detemir in Basal insulin therapy. Drugs. 2007;67(17):2557-84. [Article]
3. Tibaldi J: Actions of insulin beyond glycemic control: a perspective on insulin detemir. Adv Ther. 2007 Jul-Aug;24(4):868-82. [Article]
4. Danne T, Lupke K, Walte K, Von Schuetz W, Gall MA: Insulin detemir is characterized by a consistent pharmacokinetic profile across age-groups in children, adolescents, and adults with type 1 diabetes. Diabetes Care. 2003 Nov;26(11):3087-92. [Article]
5. Owens DR, Bolli GB: Beyond the era of NPH insulin--long-acting insulin analogs: chemistry, comparative pharmacology, and clinical application. Diabetes Technol Ther. 2008 Oct;10(5):333-49. doi: 10.1089/dia.2008.0023. [Article]
6. Donner T, Sarkar S: Insulin - Pharmacology, Therapeutic Regimens, and Principles of Intensive Insulin Therapy . [Article]
7. Morello CM: Pharmacokinetics and pharmacodynamics of insulin analogs in special populations with type 2 diabetes mellitus. Int J Gen Med. 2011;4:827-35. doi: 10.2147/IJGM.S26889. Epub 2011 Dec 12. [Article]
8. Scapin G, Dandey VP, Zhang Z, Prosise W, Hruza A, Kelly T, Mayhood T, Strickland C, Potter CS, Carragher B: Structure of the insulin receptor-insulin complex by single-particle cryo-EM analysis. Nature. 2018 Apr 5;556(7699):122-125. doi: 10.1038/nature26153. Epub 2018 Feb 28. [Article]
9. De Meyts P: The Insulin Receptor and Its Signal Transduction Network . [Article]
10. Wada T, Azegami M, Sugiyama M, Tsuneki H, Sasaoka T: Characteristics of signalling properties mediated by long-acting insulin analogue glargine and detemir in target cells of insulin. Diabetes Res Clin Pract. 2008 Sep;81(3):269-77. doi: 10.1016/j.diabres.2008.05.007. Epub 2008 Jun 27. [Article]
11. FDA Approved Drug Products: Levemir (insulin detemir) for subcutaneous injection [Link]
12. FDA Approved Drug Products: Levemir (insulin detemir) for subcutaneous injection 2022 [Link]
13. Health Canada Approved Drug Proucts: LEVEMIR® (insulin detemir) injection, for subcutaneous use [Link]

External Links

KEGG Drug

D04539

PubChem Substance

46508877

RxNav

139825

ChEMBL

CHEMBL2104391

Therapeutic Targets Database

DAP001090

PharmGKB

PA164746470

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Insulin_detemir

FDA label

Download (911 KB)

MSDS

Download (504 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Type 2 Diabetes Mellitus / Weight Gain	1
4	Completed	Diagnostic	Diabetes Mellitus	1
4	Completed	Prevention	Hyperglycemia	1
4	Completed	Treatment	Arteriosclerosis / Atherosclerosis / Type 2 Diabetes Mellitus	1
4	Completed	Treatment	Cardiovascular Disease (CVD) / Endothelial Dysfunction / Type 2 Diabetes Mellitus	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• Novo Nordisk Inc.

Dosage Forms

Form	Route	Strength
Implant	Soft tissue	14.2 mg/1mL
Injection	Subcutaneous	14.2 mg/1mL
Injection, solution	Parenteral; Subcutaneous	100 U/ML
Injection, solution	Subcutaneous	100 [iU]/1mL
Injection, solution	Subcutaneous	14.2 mg/1mL
Solution	Subcutaneous	100 U
Solution	Subcutaneous	14.2 mg
Injection	Subcutaneous
Injection, solution	Subcutaneous	100 units/mL
Injection, solution	Subcutaneous
Solution	Subcutaneous	100 unit / mL
Injection, solution	Subcutaneous	14.2 mg/ml
Injection, solution	Subcutaneous	100 U/ml
Solution	Subcutaneous	100 U/ml
Injection, solution		100 iu/1ml
Solution	Subcutaneous	100 iu/1ml

Prices

Unit description	Cost	Unit
Levemir flexpen 100 unit/ml	14.28USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US6011007	No	2000-01-04	2014-02-02
CA2171424	No	2002-06-04	2014-09-16
US8672898	Yes	2014-03-18	2022-07-02
US8684969	Yes	2014-04-01	2026-04-20
US9132239	Yes	2015-09-15	2032-08-01
US8920383	Yes	2014-12-30	2027-01-17
US7686786	No	2010-03-30	2026-08-03
US6899699	Yes	2005-05-31	2022-07-01
US5866538	Yes	1999-02-02	2017-12-20
US9108002	Yes	2015-08-18	2026-07-26
USRE41956	Yes	2010-11-23	2021-07-21
US9265893	Yes	2016-02-23	2033-03-23
US6004297	Yes	1999-12-21	2019-07-28
USRE43834	No	2012-11-27	2019-01-28
US5750497	No	1998-05-12	2019-06-16
US9486588	Yes	2016-11-08	2022-07-02
US9457154	Yes	2016-10-04	2028-03-27
USRE46363	Yes	2017-04-11	2027-02-03
US9687611	Yes	2017-06-27	2027-08-27
US9775953	Yes	2017-10-03	2027-01-17
US8579869	Yes	2013-11-12	2023-12-30
US7762994	Yes	2010-07-27	2024-11-23
US9861757	Yes	2018-01-09	2026-07-20
US9616180	Yes	2017-04-11	2026-07-20
US10220155	Yes	2019-03-05	2027-01-17
US10357616	No	2019-07-23	2026-01-20
US10376652	No	2019-08-13	2026-01-20

Properties

State

Liquid

Experimental Properties

Not Available

Targets

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Details1. Insulin receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Receptor signaling protein tyrosine kinase activity

Specific Function

Receptor tyrosine kinase which mediates the pleiotropic actions of insulin. Binding of insulin leads to phosphorylation of several intracellular substrates, including, insulin receptor substrates (...

Gene Name

INSR

Uniprot ID

P06213

Uniprot Name

Insulin receptor

Molecular Weight

156331.465 Da

References

1. Hennige AM, Sartorius T, Tschritter O, Preissl H, Fritsche A, Ruth P, Haring HU: Tissue selectivity of insulin detemir action in vivo. Diabetologia. 2006 Jun;49(6):1274-82. Epub 2006 Mar 29. [Article]
2. Kurtzhals P, Schaffer L, Sorensen A, Kristensen C, Jonassen I, Schmid C, Trub T: Correlations of receptor binding and metabolic and mitogenic potencies of insulin analogs designed for clinical use. Diabetes. 2000 Jun;49(6):999-1005. [Article]
3. Sorensen AR, Stidsen CE, Ribel U, Nishimura E, Sturis J, Jonassen I, Bouman SD, Kurtzhals P, Brand CL: Insulin detemir is a fully efficacious, low affinity agonist at the insulin receptor. Diabetes Obes Metab. 2010 Aug;12(8):665-73. doi: 10.1111/j.1463-1326.2010.01206.x. [Article]
4. Wada T, Azegami M, Sugiyama M, Tsuneki H, Sasaoka T: Characteristics of signalling properties mediated by long-acting insulin analogue glargine and detemir in target cells of insulin. Diabetes Res Clin Pract. 2008 Sep;81(3):269-77. doi: 10.1016/j.diabres.2008.05.007. Epub 2008 Jun 27. [Article]
5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Details2. Insulin-like growth factor 1 receptor

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Activator

General Function

Protein tyrosine kinase activity

Specific Function

Receptor tyrosine kinase which mediates actions of insulin-like growth factor 1 (IGF1). Binds IGF1 with high affinity and IGF2 and insulin (INS) with a lower affinity. The activated IGF1R is involv...

Gene Name

IGF1R

Uniprot ID

P08069

Uniprot Name

Insulin-like growth factor 1 receptor

Molecular Weight

154791.73 Da

References

1. Varewijck AJ, Janssen JA: Insulin and its analogues and their affinities for the IGF1 receptor. Endocr Relat Cancer. 2012 Sep 5;19(5):F63-75. doi: 10.1530/ERC-12-0026. Print 2012 Oct. [Article]

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Drug created at June 30, 2007 14:45 / Updated at August 26, 2022 21:50