Identification

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Name
Insulin Degludec
Accession Number
DB09564
Type
Biotech
Groups
Approved
Biologic Classification
Protein Based Therapies
Hormones / Insulins
Description

Insulin degludec is an ultra-long-acting form of insulin used for the treatment of hyperglycemia caused by Type 1 and Type 2 Diabetes. 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. 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. Absorption of glucose into cells allows for its transformation into glycogen or fat for storage. Insulin also inhibits hepatic glucose production, enhances protein synthesis, and inhibits lipolysis and proteolysis among many other functions.

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. As a result, people with T1D rely primarily on exogenous forms of insulin, such as insulin degludec, to lower glucose levels in the blood. 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. 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. 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.

Marketed as the brand name product Tresiba, insulin degludec has a duration of action up to 42 hours allowing for once-daily dosing, typically at bedtime. Due to its duration of action, Tresiba is considered "basal insulin" as it provides low concentrations of background insulin that can keep blood sugar stable between meals or overnight. Basal insulin is often combined with short-acting "bolus insulin" such as Insulin lispro, Insulin Glulisine, or Insulin aspart to provide higher doses of insulin required following meals. 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.

Compared to endogenous insulin, insulin degludec has an added hexadecanedioic acid on lysine at the B29 position which allows for the formation of multi-hexamers. When injected subcutaneously, these multi-hexamers form a drug depot store from which monomers are slowly and continuously absorbed into the circulation. As a result, Insulin Degludec has a protracted time action profile due to the delayed absorption from subcutaneous tissue depots into the systemic circulation. Compared to available long-acting analogues such as Insulin glargine and Insulin detemir, which have a duration of action of 20-24 hours, insulin degludec provides a consistent level of basal insulin over 42 hours with a low peak:trough ratio. Limitations of shorter acting analogues include more frequent dosing and less stable pharmacokinetics, which may negatively impact patient adherence and glucose control, particularly nocturnal control.

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. 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.

Insulin Degludec was approved by the FDA in September 2015 as the product Tresiba, for use in providing glycemic control to adults with diabetes mellitus.

Protein structure
Db09564
Protein chemical formula
C274H411N65O81S6
Protein average weight
6103.97 Da
Sequences
>A Chain
FVNQHLCGSHLVEALYLVCGERGFFYTPK
>B Chain
GIVEQCCTSICSLYQLENYCN
Download FASTA Format
Synonyms
  • Insulina degludec
External IDs
NN-1250 / NN1250
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TresibaSolution200 unitSubcutaneousNovo Nordisk2017-09-15Not applicableCanada
TresibaInjection, solution200 U/1mLSubcutaneousA-S Medication Solutions2015-09-25Not applicableUs
TresibaInjection, solution200 U/mlSubcutaneousNovo Nordisk2013-01-21Not applicableEu
TresibaInjection, solution100 U/mlSubcutaneousNovo Nordisk2013-01-21Not applicableEu
TresibaSolution100 unitSubcutaneousNovo Nordisk2017-09-15Not applicableCanada
TresibaInjection, solution200 U/mlSubcutaneousNovo Nordisk2013-01-21Not applicableEu
TresibaInjection, solution100 U/mlSubcutaneousNovo Nordisk2013-01-21Not applicableEu
TresibaInjection, solution100 U/mlSubcutaneousNovo Nordisk2013-01-21Not applicableEu
TresibaInjection, solution100 U/1mLSubcutaneousNovo Nordisk2018-11-21Not applicableUs
TresibaInjection, solution200 U/mlSubcutaneousNovo Nordisk2013-01-21Not applicableEu
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
RyzodegInsulin Degludec (2.56 mg/ml) + Insulin aspart (1.05 mg/ml)Injection, solutionSubcutaneousNovo Nordisk2013-01-21Not applicableEu
RyzodegInsulin Degludec (2.56 mg/ml) + Insulin aspart (1.05 mg/ml)Injection, solutionSubcutaneousNovo Nordisk2013-01-21Not applicableEu
RyzodegInsulin Degludec (2.56 mg/ml) + Insulin aspart (1.05 mg/ml)Injection, solutionSubcutaneousNovo Nordisk2013-01-21Not applicableEu
RyzodegInsulin Degludec (2.56 mg/ml) + Insulin aspart (1.05 mg/ml)Injection, solutionSubcutaneousNovo Nordisk2013-01-21Not applicableEu
RyzodegInsulin Degludec (2.56 mg/ml) + Insulin aspart (1.05 mg/ml)Injection, solutionSubcutaneousNovo Nordisk2013-01-21Not applicableEu
RyzodegInsulin Degludec (2.56 mg/ml) + Insulin aspart (1.05 mg/ml)Injection, solutionSubcutaneousNovo Nordisk2013-01-21Not applicableEu
RyzodegInsulin Degludec (2.56 mg/ml) + Insulin aspart (1.05 mg/ml)Injection, solutionSubcutaneousNovo Nordisk2013-01-21Not applicableEu
Ryzodeg 70/30Insulin Degludec (70 U/1mL) + Insulin aspart (30 U/1mL)Injection, solutionSubcutaneousNovo Nordisk2018-01-012018-01-01Us
XultophyInsulin Degludec (100 unit) + Liraglutide (3.6 mg)SolutionSubcutaneousNovo Nordisk2018-06-06Not applicableCanada
XultophyInsulin Degludec (100 U/ml) + Liraglutide (3.6 mg/ml)Injection, solutionSubcutaneousNovo Nordisk2014-09-18Not applicableEu
Categories
UNII
54Q18076QB
CAS number
844439-96-9

Pharmacology

Indication

Insulin degludec is indicated to improve glycemic control in patients 1 year of age and older with diabetes mellitus.

Associated Conditions
Pharmacodynamics

Insulin is a natural hormone produced by beta cells of the pancreas. In non-diabetic individuals, the pancreas produces a continuous supply of low levels of basal insulin along with spikes of insulin 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 the 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 detemir is a long-acting insulin analogue with a flat and predictable action profile. 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. Interestingly, it has a lower affinity (30%) for the insulin receptor than human insulin.

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. 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 signalling 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.

TargetActionsOrganism
AInsulin receptor
ligand
Humans
UInsulin-like growth factor 1 receptorNot AvailableHumans
Additional Data Available
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Contraindications

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Absorption

In patients with type 1 diabetes, after 8 days of once daily subcutaneous dosing with 0.4 U/kg, maximum degludec concentrations of 4472 pmol/L were attained at a median of 9 hours (tmax). After the first dose of, median onset of appearance was around one hour. The glucose lowering effect lasted at least 42 hours after the last of 8 once-daily injections. Insulin degludec concentration reach steady state levels after 3-4 days.

Volume of distribution
Not Available
Protein binding

The affinity of insulin degludec to serum albumin corresponds to a plasma protein binding of >99% in human plasma. The results of the in vitro protein binding studies demonstrate that there is no clinically relevant interaction between insulin degludec and other protein bound drugs.

Metabolism

All insulin degludec metabolites are inactive.

Route of elimination
Not Available
Half life

The half-life after subcutaneous administration is determined primarily by the rate of absorption from the subcutaneous tissue. On average, the half-life at steady state is approximately 25 hours independent of dose.

Clearance

The mean apparent clearance of insulin degludec is 0.03 L/kg (2.1 L/h in 70 kg individual) after single subcutaneous dose of 0.4 units/kg.

Toxicity

Observe for signs and symptoms of hypoglycemia, hypokalemia, and fluid retention and heart failure with concomitant use of Thiazolidinediones. Pregnancy Category C

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Insulin Degludec.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Insulin Degludec is combined with 2,4-thiazolidinedione.
5-(2-methylpiperazine-1-sulfonyl)isoquinolineThe therapeutic efficacy of Insulin Degludec can be increased when used in combination with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Insulin Degludec.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypoglycemic activities of Insulin Degludec.
8-azaguanineThe metabolism of 8-azaguanine can be increased when combined with Insulin Degludec.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be increased when combined with Insulin Degludec.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be increased when combined with Insulin Degludec.
9-MethylguanineThe metabolism of 9-Methylguanine can be increased when combined with Insulin Degludec.
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Insulin Degludec.
Additional Data Available
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    Severity

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    Action

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Food Interactions
Not Available

References

General References
  1. Garber AJ, King AB, Del Prato S, Sreenan S, Balci MK, Munoz-Torres M, Rosenstock J, Endahl LA, Francisco AM, Hollander P: Insulin degludec, an ultra-longacting basal insulin, versus insulin glargine in basal-bolus treatment with mealtime insulin aspart in type 2 diabetes (BEGIN Basal-Bolus Type 2): a phase 3, randomised, open-label, treat-to-target non-inferiority trial. Lancet. 2012 Apr 21;379(9825):1498-507. doi: 10.1016/S0140-6736(12)60205-0. [PubMed:22521072]
  2. Wang F, Surh J, Kaur M: Insulin degludec as an ultralong-acting basal insulin once a day: a systematic review. Diabetes Metab Syndr Obes. 2012;5:191-204. doi: 10.2147/DMSO.S21979. Epub 2012 Jul 5. [PubMed:22826637]
  3. Haahr H, Heise T: A review of the pharmacological properties of insulin degludec and their clinical relevance. Clin Pharmacokinet. 2014 Sep;53(9):787-800. doi: 10.1007/s40262-014-0165-y. [PubMed:25179915]
  4. Jonassen I, Havelund S, Hoeg-Jensen T, Steensgaard DB, Wahlund PO, Ribel U: Design of the novel protraction mechanism of insulin degludec, an ultra-long-acting basal insulin. Pharm Res. 2012 Aug;29(8):2104-14. doi: 10.1007/s11095-012-0739-z. Epub 2012 Apr 7. [PubMed:22485010]
  5. Thuillier P, Alavi Z, Kerlan V: Long-term safety and efficacy of insulin degludec in the management of type 2 diabetes. Diabetes Metab Syndr Obes. 2015 Oct 1;8:483-93. doi: 10.2147/DMSO.S54953. eCollection 2015. [PubMed:26457056]
External Links
KEGG Drug
D09727
PubChem Substance
347910463
ChEMBL
CHEMBL2107869
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
ATC Codes
A10AD06 — Insulin degludec and insulin aspartA10AE56 — Insulin degludec and liraglutideA10AE06 — Insulin degludec
AHFS Codes
  • 68:20.08.16 — Long-acting Insulins
FDA label
Download (7.77 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentDiabetes Mellitus (DM) / Healthy Volunteers13
1CompletedTreatmentDiabetes Mellitus (DM) / Healthy Volunteers / Type 2 Diabetes Mellitus1
1CompletedTreatmentDiabetes Mellitus (DM) / Type 1 Insulin-Dependent Diabetes Mellitus22
1CompletedTreatmentDiabetes Mellitus (DM) / Type 1 Insulin-Dependent Diabetes Mellitus / Type 2 Diabetes Mellitus3
1CompletedTreatmentDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus6
1CompletedTreatmentHealthy Volunteers1
1TerminatedTreatmentDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus1
2Active Not RecruitingTreatmentType 2 Diabetes Mellitus1
2CompletedTreatmentDiabetes Mellitus (DM) / Type 1 Insulin-Dependent Diabetes Mellitus2
2CompletedTreatmentDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus4
2RecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
2, 3RecruitingTreatmentType 2 Diabetes Mellitus1
3Active Not RecruitingTreatmentDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus1
3CompletedTreatmentDiabetes Mellitus (DM) / Type 1 Insulin-Dependent Diabetes Mellitus10
3CompletedTreatmentDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus46
3CompletedTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
3CompletedTreatmentType 2 Diabetes Mellitus1
3RecruitingTreatmentDiabetes Mellitus (DM)1
3RecruitingTreatmentDiabetes Mellitus (DM) / Type 1 Insulin-Dependent Diabetes Mellitus1
3RecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
3RecruitingTreatmentType 2 Diabetes Mellitus3
4Active Not RecruitingTreatmentType 2 Diabetes Mellitus1
4CompletedTreatmentNocturnal Hypoglycemia / Recurrent Severe Hypoglycaemia / Type 1 Insulin-Dependent Diabetes Mellitus1
4CompletedTreatmentType 2 Diabetes Mellitus4
4Enrolling by InvitationTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
4Not Yet RecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
4Not Yet RecruitingTreatmentType2 Diabetes1
4RecruitingTreatmentType 1 Insulin-Dependent Diabetes Mellitus2
4RecruitingTreatmentType 2 Diabetes Mellitus2
Not AvailableActive Not RecruitingNot AvailableType 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableDiabetes Mellitus (DM)2
Not AvailableCompletedNot AvailableDiabetes Mellitus (DM) / Type 1 Insulin-Dependent Diabetes Mellitus / Type 2 Diabetes Mellitus4
Not AvailableCompletedNot AvailableDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableType 1 Insulin-Dependent Diabetes Mellitus1
Not AvailableCompletedNot AvailableType 1 Insulin-Dependent Diabetes Mellitus / Type 2 Diabetes Mellitus1
Not AvailableEnrolling by InvitationNot AvailableDiabetes Mellitus (DM) / Type 1 Insulin-Dependent Diabetes Mellitus / Type 2 Diabetes Mellitus1
Not AvailableEnrolling by InvitationNot AvailableType 2 Diabetes Mellitus3
Not AvailableNot Yet RecruitingNot AvailableDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, solutionSubcutaneous100 U/1mL
Injection, solutionSubcutaneous100 U/ml
Injection, solutionSubcutaneous200 U/1mL
Injection, solutionSubcutaneous200 U/ml
SolutionSubcutaneous100 unit
SolutionSubcutaneous200 unit
Injection, solutionSubcutaneous
SolutionSubcutaneous
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8672898Yes2014-03-182022-07-02Us
US8684969Yes2014-04-012026-04-20Us
US9132239Yes2015-09-152032-08-01Us
US8920383Yes2014-12-302027-01-17Us
US7686786No2010-03-302026-08-03Us
US6899699Yes2005-05-312022-07-01Us
US5866538Yes1999-02-022017-12-20Us
US9108002Yes2015-08-182026-07-26Us
US6458924No2002-10-012017-08-22Us
US6268343Yes2001-07-312023-02-22Us
US8846618Yes2014-09-302022-12-27Us
US7235627No2007-06-262017-08-22Us
US7615532Yes2009-11-102029-12-28Us
US9486588Yes2016-11-082022-07-02Us
US9457154Yes2016-10-042028-03-27Us
USRE46363Yes2017-04-112027-02-03Us
US8937042Yes2015-01-202029-11-05Us
US9687611Yes2017-06-272027-08-27Us
US9775953Yes2017-10-032027-01-17Us
US8579869Yes2013-11-122023-12-30Us
US7762994Yes2010-07-272024-11-23Us
US9884094No2018-02-062033-05-01Us
US9861757Yes2018-01-092026-07-20Us
US9616180Yes2017-04-112026-07-20Us
US10220155Yes2019-03-052027-01-17Us
US10357616No2006-01-202026-01-20Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Liquid
Experimental Properties
Not Available

Taxonomy

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

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
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
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Wang F, Surh J, Kaur M: Insulin degludec as an ultralong-acting basal insulin once a day: a systematic review. Diabetes Metab Syndr Obes. 2012;5:191-204. doi: 10.2147/DMSO.S21979. Epub 2012 Jul 5. [PubMed:22826637]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Barnett CR, Wilson J, Wolf CR, Flatt PR, Ioannides C: Hyperinsulinaemia causes a preferential increase in hepatic P4501A2 activity. Biochem Pharmacol. 1992 Mar 17;43(6):1255-61. doi: 10.1016/0006-2952(92)90500-i. [PubMed:1562279]
  2. Pass GJ, Becker W, Kluge R, Linnartz K, Plum L, Giesen K, Joost HG: Effect of hyperinsulinemia and type 2 diabetes-like hyperglycemia on expression of hepatic cytochrome p450 and glutathione s-transferase isoforms in a New Zealand obese-derived mouse backcross population. J Pharmacol Exp Ther. 2002 Aug;302(2):442-50. doi: 10.1124/jpet.102.033553. [PubMed:12130701]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da

Drug created on November 30, 2015 12:10 / Updated on November 11, 2019 07:04