Insulin glulisine

Short description: Rapid-acting insulin analogue

Insulin glulisine

PDB: 6gv0​

Clinical data
Trade names| Apidra, Apidra Solostar
AHFS/Drugs.com| Monograph
MedlinePlus| a607033
License data|

* US DailyMed: glulisine Insulin glulisine

Pregnancy
category|

* AU: B3[1]

Routes of
administration| Subcutaneous, intravenous
ATC code|

* A10AB06 (WHO)

Legal status
Legal status|

* AU: S4 (Prescription only)
* UK: POM (Prescription only)
* US: ℞-only [2]
* EU: Rx-only [3]

Identifiers
CAS Number|

* 207748-29-6 N

DrugBank|

* DB01309 Y

ChemSpider|

* none

UNII|

* 7XIY785AZD

KEGG|

* D04540 Y

PDB ligand|

* 6gv0 (PDBe, RCSB PDB)

Chemical and physical data
Formula| C258H384N64O78S6
Molar mass| 5822.64 g·mol−1
NY (what is this?) (verify)

Insulin glulisine, sold under the brand name Apidra among others, is a rapid-acting modified form of medical insulin used for the treatment of diabetes. It differs from human insulin in that the amino acid asparagine at position B3 is replaced by lysine and the lysine in position B29 is replaced by glutamic acid.[2] When injected subcutaneously, it appears in the blood earlier than regular human insulin (RHI).[4] Intravenous injections may be used for extreme hyperglycemia.[2] It was developed by Sanofi-Aventis.

The most common side effects include hypoglycaemia (low blood glucose levels).[3]

Insulin glulisine was approved for medical use in the United States[2][5] and in the European Union[3] in 2004.

## Medical uses

Insulin glulisine is indicated for the treatment of diabetes.[2][3]

## Mechanism behind the rapid bioavailability

The monomer-monomer interactions are weaker in insulin glulisin compared to unmodified human insulin, and therefore, it does not as readily form dimers and hexamers, which are dominant in unmodified insulin. Due to their large size, insulin hexamers need to break up into dimers or monomers before they are able to enter the blood and become biologically active. Specifically, the B3 mutation causes electrostatic repulsion in the hexamer to arginine-22 in the B chain of other insulin molecules in the same hexamer, while the B29 mutation causes fewer hydrogen bonds to stabilize the dimer. Furthermore, the isoelectric point of insulin glulisine insulin, which is shifted from 5.5 (of unmodified human insulin) to 5.1, increases the solubility at physiological pH levels.[6]

## References

1. ↑ "Insulin glulisine Use During Pregnancy". 6 April 2020. https://www.drugs.com/pregnancy/insulin-glulisine.html.
2. ↑ 2.0 2.1 2.2 2.3 2.4 "Apidra- insulin glulisine injection, solution; Apidra Solostar- insulin glulisine injection, solution". 25 July 2023. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e7af6a7a-8046-4fb4-9979-4ec4230b23aa.
3. ↑ 3.0 3.1 3.2 3.3 "Apidra EPAR". 27 July 2009. https://www.ema.europa.eu/en/medicines/human/EPAR/apidra.
4. ↑ "Insulin glulisine: a review of its use in the management of diabetes mellitus". Drugs 69 (8): 1035–57. May 2009. doi:10.2165/00003495-200969080-00006. PMID 19496630.
5. ↑ "Drug Approval Package: Apidra (Insulin Glulisine [rDNA Origin) NDA #021629"]. https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-629_Apidra.cfm.
6. ↑ "Analysis of Insulin Glulisine at the Molecular Level by X-Ray Crystallography and Biophysical Techniques". Scientific Reports 11 (1): 1737. January 2021. doi:10.1038/s41598-021-81251-2. PMID 33462295. Bibcode: 2021NatSR..11.1737G.

* v
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* e

Oral anti-diabetic drugs, insulins and insulin analogs, and other drugs used in diabetes (A10)

Insulin|

| Sensitizers|

| Biguanides|

* Buformin‡
* Metformin#
* Phenformin‡

|

TZDs/"glitazones" (PPAR)|

* Ciglitazone§
* Darglitazone§
* Englitazone§
* Lobeglitazone
* Netoglitazone§
* Pioglitazone
* Rivoglitazone†
* Rosiglitazone
* Troglitazone‡

Dual PPAR agonists|

* Aleglitazar†
* Muraglitazar§
* Saroglitazar
* Tesaglitazar§

Secretagogues|

| K+ATP|

| Sulfonylureas|

* 1st generation: Acetohexamide
* Carbutamide
* Chlorpropamide
* Glycyclamide
* Metahexamide
* Tolazamide
* Tolbutamide

* 2nd generation: Glibenclamide (glyburide)
* Glibornuride
* Glicaramide
* Gliclazide#
* Glimepiride
* Glipizide
* Gliquidone
* Glisoxepide
* Glyclopyramide

|

Meglitinides/"glinides"|

* Mitiglinide
* Nateglinide
* Repaglinide

GLP-1 receptor agonists|

* Albiglutide‡
* Dulaglutide
* Exenatide
* Liraglutide
* Lixisenatide
* Semaglutide
* Taspoglutide†

DPP-4 inhibitors/"gliptins"|

* Alogliptin
* Anagliptin
* Evogliptin
* Garvagliptin
* Gemigliptin
* Gosogliptin
* Linagliptin
* Melogliptin
* Omarigliptin
* Saxagliptin
* Sitagliptin
* Teneligliptin
* Trelagliptin
* Vildagliptin

Free fatty acid receptor 1 (GPR40)|

* Fasiglifam†

Analogs/other insulins|

* fast-acting
* Insulin aspart
* Insulin glulisine
* Insulin lispro
* short-acting
* Regular insulin
* long-acting
* Insulin detemir
* Insulin glargine (+lixisenatide)
* NPH insulin
* ultra-long-acting
* Insulin degludec (+liraglutide)
* inhalable
* Exubera‡
* Afrezza

Other|

| Aldose reductase inhibitors|

* Epalrestat
* Fidarestat§
* Ranirestat†
* Tolrestat‡
* Zenarestat§

|

Alpha-glucosidase inhibitors|

* Acarbose
* Miglitol
* Voglibose

Amylin analog|

* Pramlintide

Sodium glucose transporter (SGLT2) inhibitors/"gliflozins"|

* Canagliflozin
* Dapagliflozin
* Empagliflozin
* Ertugliflozin
* Ipragliflozin
* Remogliflozin§
* Sergliflozin§
* Tofogliflozin†

Other|

* Benfluorex‡
* Bromocriptine

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

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