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Menadione | CAS No: 58-27-5 | GMP-certified suppliers
A medication that supports normal blood clotting and bone calcification by serving as a synthetic precursor to active vitamin K forms used in coagulation and nutritional therapies.
Therapeutic categories
Primary indications
- The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification
Product Snapshot
- Menadione is supplied as an injectable solution formulation
- It is primarily used for supporting normal blood clotting and bone calcification processes
- Menadione is approved for use as a nutraceutical product in key regulatory markets
Clinical Overview
Clinically, vitamin K compounds are primarily indicated for their essential role in blood coagulation. Vitamin K is a critical cofactor in the gamma-carboxylation of glutamic acid residues on vitamin K-dependent proteins including clotting factors II, VII, IX, and X, as well as anticoagulant proteins C and S. This posttranslational modification is catalyzed by gamma-carboxylase enzymes and requires the reduced form of vitamin K (vitamin K hydroquinone) for activity. Additionally, vitamin K contributes to bone metabolism through gamma-carboxylation of osteocalcin and matrix Gla protein, which are involved in bone matrix formation and calcification.
Pharmacodynamically, menadione serves as a fat-soluble vitamin precursor, converted mainly within the liver to menaquinone. Unlike natural vitamin K1 (phylloquinone) synthesized by plants or vitamin K2 produced by gut bacteria, menadione is a synthetic analogue. Despite its utility, menadione use is limited due to safety concerns; notably, excessive doses, particularly in neonates, can precipitate kernicterus, a serious neurotoxic condition caused by elevated bilirubin crossing the blood-brain barrier.
Key safety considerations include the risk of dose-dependent toxicity and potential interactions due to modulation of cytochrome P450 enzymes, influencing metabolism of concomitant drugs.
In pharmaceutical development and regulatory contexts, menadione is classified among approved nutraceuticals and plays roles within multiple drug categories related to coagulation modulation and vitamin supplementation. Quality control for menadione APIs should focus on rigorous purity assessment, control of residual solvents, and verification of synthetic origin to ensure batch-to-batch consistency. Suppliers must comply with pharmacopeial standards and regulatory requirements to support safe and effective downstream utilization in vitamin K formulations and nutritional supplements.
Identification & chemistry
| Generic name | Menadione |
|---|---|
| Molecule type | Small molecule |
| CAS | 58-27-5 |
| UNII | 723JX6CXY5 |
| DrugBank ID | DB00170 |
Pharmacology
| Summary | Menadione (vitamin K3) is a synthetic precursor converted in vivo to active vitamin K2, serving as a cofactor for gamma-carboxylation of glutamic acid residues on vitamin K-dependent proteins. These proteins include coagulation factors II, VII, IX, and X, as well as anticoagulant proteins C and S, which collectively regulate hemostasis. Menadione also supports gamma-carboxylation of bone-related proteins, such as osteocalcin, implicating a role in bone metabolism. |
|---|---|
| Mechanism of action | Menadione (vitamin K3) is involved as a cofactor in the posttranslational gamma-carboxylation of glutamic acid residues of certain proteins in the body. These proteins include the vitamin K-dependent coagulation factors II (prothrombin), VII (proconvertin), IX (Christmas factor), X (Stuart factor), protein C, protein S, protein Zv and a growth-arrest-specific factor (Gas6). In contrast to the other vitamin K-dependent proteins in the blood coagulation cascade, protein C and protein S serve anticoagulant roles. The two vitamin K-dependent proteins found in bone are osteocalcin, also known as bone G1a (gamma-carboxyglutamate) protein or BGP, and the matrix G1a protein or MGP. Gamma-carboxylation is catalyzed by the vitamin K-dependent gamma-carboxylases. The reduced form of vitamin K, vitamin K hydroquinone, is the actual cofactor for the gamma-carboxylases. Proteins containing gamma-carboxyglutamate are called G1a proteins. |
| Pharmacodynamics | Menadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K. The former, which is also known as phylloquinone, is synthesized by plants and can be found in such foods as spinach, broccoli, lettuce, and soybeans. The latter, sometimes alternatively referred to as menaquinone, is primarily produced by bacteria in the anterior part of the gut and the intestines. Vitamin K3, on the other hand, is one of the many manmade versions of vitamin K. Also called menadione, this yellowish, synthetic crystalline substance is converted into the active form of the K2 vitamin inside of the animal body. While a vitamin K deficiency can be dangerous, especially to infants that may easily suffer from extensive hemorrhaging, an overdose can be as equally detrimental. Newborns that are administered too great a dosage of vitamin K3 can suffer from kernicterus, a form of severe brain damage that may produce decreased movement, loss of appetite, seizures, deafness, mental retardation, and even death. This condition is associated with an abnormally high concentration of bilirubin, a bile pigment, in the tissues of the brain, which can be caused by the presence of K3. For this reason, K3 is less often utilized medically than it was in former times. |
Targets
| Target | Organism | Actions |
|---|---|---|
| Vitamin K-dependent gamma-carboxylase | Humans | cofactor |
| Vitamin K epoxide reductase complex subunit 1 | Humans | cofactor |
| Vitamin K epoxide reductase complex subunit 1-like protein 1 | Humans | cofactor |
ADME / PK
| Absorption | Variable and ranges from 10% to 80% |
|---|---|
| Metabolism | Hepatic |
Formulation & handling
- Menadione is a small molecule naphthoquinone primarily formulated for injectable solutions.
- The compound exhibits moderate water solubility and a logP suggesting limited but sufficient aqueous bioavailability for parenteral formulations.
- Handling should consider potential sensitivity to oxidation due to the quinone moiety, indicating the need for protected storage conditions.
Regulatory status
Supply Chain
| Supply chain summary | Menadione is manufactured by Eli Lilly and Co, with packaging handled by Spectrum Pharmaceuticals. The product has a presence in multiple markets including the US and EU. Patent expiration indicates that generic competition may already exist or could emerge in the near term. |
|---|
Safety
| Toxicity | Menadione (vitamin K3), which is not used as a nutritional supplemental form of vitamin K for humans, has been reported to cause adverse reactions, including hemolytic anemia. Large doses have also been reported to cause brain damage. |
|---|
- 1
- Menadione has been associated with hemolytic anemia and central nervous system toxicity at elevated exposure levels
- 2
Menadione is a type of Vitamins
Vitamins are an essential subcategory of pharmaceutical Active Pharmaceutical Ingredients (APIs) that play a crucial role in maintaining optimal health and well-being. These organic compounds are required in small quantities by the human body to support various metabolic processes and ensure proper functioning of bodily systems. Vitamins can be broadly classified into two groups: fat-soluble vitamins (such as vitamins A, D, E, and K) and water-soluble vitamins (including vitamin C and B-complex vitamins). Each vitamin has a specific role and function within the body.
Pharmaceutical APIs in the vitamin subcategory are carefully synthesized or extracted to meet stringent quality standards and ensure purity, efficacy, and safety. They are used as active ingredients in the formulation of various pharmaceutical products, including dietary supplements, fortified foods, and pharmaceutical formulations.
Vitamin APIs are commonly utilized in the pharmaceutical industry for their therapeutic benefits. For instance, vitamin D API is widely prescribed to treat deficiencies and maintain optimal bone health, while vitamin C API is utilized for its antioxidant properties and immune-boosting effects. B-complex vitamins, such as vitamin B12 API, are essential for energy production and nerve function.
Overall, vitamins are integral to maintaining good health, and pharmaceutical APIs in this subcategory play a vital role in providing these essential nutrients to individuals through various pharmaceutical and dietary applications.
Menadione (Vitamins), classified under Therapeutic Nutrients/Minerals/Electrolyte
Therapeutic Nutrients/Minerals/Electrolytes: A Comprehensive Technical DescriptionTherapeutic nutrients, minerals, and electrolytes are a vital category of pharmaceutical active pharmaceutical ingredients (APIs) used to support and enhance overall health and well-being. These compounds play a crucial role in maintaining the body's physiological balance, aiding in various metabolic processes, and addressing specific deficiencies.
Therapeutic nutrients encompass a broad range of substances, including vitamins, minerals, and electrolytes. Vitamins are organic compounds required in small quantities for proper bodily functions and are essential for growth, development, and disease prevention. Minerals, on the other hand, are inorganic substances that support numerous physiological processes, such as bone formation, nerve function, and energy production.
Electrolytes are minerals that carry an electric charge when dissolved in bodily fluids, including sodium, potassium, calcium, magnesium, and chloride. They play a crucial role in maintaining proper hydration, nerve impulses, muscle contractions, and pH balance.
Pharmaceutical APIs in the Therapeutic Nutrients/Minerals/Electrolyte category are designed to address specific deficiencies or imbalances in the body. These APIs are often used in the formulation of dietary supplements, nutritional products, and therapeutic treatments. They are manufactured under stringent quality control guidelines to ensure purity, potency, and bioavailability.
Therapeutic nutrients/minerals/electrolytes APIs are available in various forms, including tablets, capsules, powders, and liquid formulations. They are formulated to meet specific dosage requirements and can be combined with other ingredients for targeted health benefits.
Overall, therapeutic nutrients, minerals, and electrolytes APIs are essential components in maintaining optimal health. Their use helps address deficiencies, support bodily functions, and promote overall well-being. Pharmaceutical companies and healthcare professionals rely on these high-quality APIs to develop effective and safe products that contribute to a healthier population.
Menadione API manufacturers & distributors
Compare qualified Menadione API suppliers worldwide. We currently have 4 companies offering Menadione API, with manufacturing taking place in 3 different countries. Use the table below to review supplier type, countries of origin, certifications, product portfolio and GMP audit availability.
| Supplier | Type | Country | Product origin | Certifications | Portfolio |
|---|---|---|---|---|---|
| Apollo Healthcare Resourc... | Distributor | Singapore | Singapore | BSE/TSE, CEP, CoA, EDMF/ASMF, FDA, GMP, ISO9001, JDMF, KDMF, MSDS, USDMF, WC | 200 products |
| Arshine Pharmaceutical Co... | Distributor | China | China | BSE/TSE, CEP, CoA, FDA, GMP, MSDS, USDMF | 176 products |
| Menadiona, S.L. | Producer | Spain | Spain | BSE/TSE, CoA, ISO9001, MSDS | 15 products |
| Sinoway industrial Co.,Lt... | Distributor | China | China | BSE/TSE, CoA, MSDS | 757 products |
When sending a request, specify which Menadione API quality you need: for example EP (Ph. Eur.), USP, JP, BP, or another pharmacopoeial standard, as well as the required grade (base, salt, micronised, specific purity, etc.).
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